ACCEPTED MANUSCRIPT
Characterization data of compounds 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3v and 3x were found
exactly similar as reported in the literature (References of above compound are mentioned in
Supplementary data).
3-Hydroxy-1-methoxy-6-methyl-9H-fluoren-9-one (3m)
Yellow Powder: 0.284 g, 80 % isolated yield; 1H NMR (400 MHz, CDCl3): δ 9.45 (s, 1H), 7.64(d, J= 7.3
MHz, 1H), 7.57(s,1H), 7.24(d, J= 7.5 MHz, 1H), 6.91(s,1H), 6.39(s,1H), 3.81(s,3H), 2.35(s,3H); 13C
NMR (100 MHz, CDCl3): δ 197.15, 165.31, 163.56, 147.30, 146.22, 145.91, 134.40, 129.49, 125.84,
123.88, 114.48, 103.26, 99.26, 50.79, 21.21; FT-IR (KBr, cm-1) 3080, 2950, 1752, 1220, 1050. Anal.
Calcd. For C15H12O3: C: 83.10; H: 3.92. Found: C: 83.11; H: 3.91. mp 135-137 °C. HRMS-ESI (m/z)
calcd for C15H12O3 [M + H]+ 241.0864, found 241.0862.
3-Hydroxy-1,6-dimethyl-9H-fluoren-9-one (3n)
1
Yellow Powder: 0.282 g, 83 % isolated yield; H NMR (400 MHz, CDCl3): δ 9.45 (s, 1H), 7.63-7.57(m,
2H), 7.24(d, J= 7.1 MHz, 1H), 7.10(s,1H), 6.69(s,1H), 2.53(s,3H), 2.35(s,3H); 13C NMR (100 MHz,
CDCl3): δ 200.02, 162.26, 147.30, 149.91, 144.29, 142.19, 134.40, 129.49, 125.84, 123.88, 122.72,
117.01, 108.02, 21.21, 20.73; FT-IR (KBr, cm-1) 3090, 3020, 2970, 2950, 1750, 1215. Anal. Calcd. For
C15H12O2: C: 80.34; H: 5.39. Found: C: 80.37; H: 5.38. mp 123-124 °C. HRMS-ESI (m/z) calcd for
C15H12O2 [M + H]+ 225.0915, found 225.0917.
3-Methoxy-1,5-dimethyl-9H-fluoren-9-one (3o)
1
Light yellow Powder: 0.284 g, 80 % isolated yield; H NMR (400 MHz, CDCl3): δ 7.57(s, 1H), 7.36-
7.34(m, 2H), 7.20(s, 1H), 6.75(s, 1H), 3.81(s, 3H), 2.54(s, 3H), 2.47(s, 3H); 13C NMR (100 MHz,
CDCl3): δ 200.64, 164.44, 147.85, 140.82, 139.91, 136.81, 135.66, 130.71, 128.49, 124.02, 123.03,
116.00, 104.46, 56.04, 20.73, 20.58; FT-IR (KBr, cm-1) 3020, 2960, 2870, 1740, 1030. Anal. Calcd. For
C16H14O2: C: 80.65; H: 5.92. Found: C: 80.63; H: 5.91. mp 127-130 °C. HRMS-ESI (m/z) calcd for
C16H14O2 [M + H]+ 239.1072, found 239.1071.
1-Chloro-6-fluoro-3-methoxy-9H-fluoren-9-one (3p)
Pale yellow Powder: 0.302 g, 80 % isolated yield; mp 183-187 0C; 1H NMR (400 MHz, CDCl3): δ 7.68(s,
13
1H), 7.46(s, 1H), 7.24(s, 1H), 7.13(d, J= 7.5 MHz, 1H), 6.95(s, 1H), 3.81(s, 3H); C NMR (100 MHz,
CDCl3): δ 193.28, 169.68 (d, JCF=152.3 Hz), 164.32, 148.34, 143.26, 137.77, 130.90, 128.49, 128.45,
114.74, 114.65, 109.78, 104.70, 56.04; FT-IR (KBr, cm-1) 3070, 1745, 1230, 1025, 820. Anal. Calcd. For
C14H8ClFO2: C: 64.02; H: 3.07. Found: C: 64.03; H: 3.06. HRMS-ESI (m/z) calcd for C14H8ClFO2 [M +
H]+ 263.0275, found 263.0272.
1-Ethoxy-6-methyl-9H-fluoren-9-one (3q)
0
Light brown Powder: 0.263 g, 74 % isolated yield; mp 97-99 C; 1H NMR (400 MHz, CDCl3): δ 7.63(s,
1H), 7.57(m, 2H), 7.41(d, J= 6.9 MHz, 1H), 7.24(d, J= 7.4 MHz, 1H), 7.13(d, J= 7.3 MHz, 1H), 4.06 (q, J
= 7.4 MHZ , 2H), 2.35(s, 3H), 1.39(t, J= 7.0 MHz, 3H); 13C NMR (100 MHz, CDCl3): δ 197.25, 160.05,
147.20, 146.36, 145.23, 135.27, 134.83, 129.11, 125.86, 123.54, 122.21, 115.15, 114.14, 64.32, 21.21,
13.83; FT-IR (KBr, cm-1) 3040, 2950, 2860, 1750, 1040. Anal. Calcd. For C16H14O2: C: 80.65; H: 5.92.
Found: C: 80.64; H: 5.91. HRMS-ESI (m/z) calcd for C16H14O2 [M + H]+ 239.1072, found 239.1074.
14