The Journal of Organic Chemistry
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white solid (71 mg, 80%): mp 104−106 °C; H NMR (300
MHz, CDCl3) δ 7.55 (d, J = 8.7 Hz, 2H), 7.23 – 7.20 (m, 2H),
7.06 (t, J = 4.8 Hz, 1H), 6.92 (d, J = 8.7 Hz, 2H), 3.84 (s,
3H); 13C {1H} NMR (75 MHz, CDCl3) δ 159.3, 144.5, 128.0,
127.4, 127.3, 124.0, 122.2, 114.4, 55.5.
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(11) The combination of HFIP with a quaternary ammonium
salts as deep eutectic solvents (DESs) for the halogenation of
boron dipyrromethene has been reported. Wang, L.; Zhu, K.-q.;
Chen, Q.; He, M.-y. Dyes and Pigments 2015, 112, 274.
N-([1,1'-biphenyl]-4-yl)acetamide (13g).32 The title com-
pound was prepared as described in the general proce-
dure using acetanilide (67.5 mg, 0.5 mmol), NIS (112.0 mg,
0.5 mmol) and phenylboronic acid (91.5 mg, 0.75 mmol),
and purified by using 30 % EtOAc in cyclohexane as a
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white solid (98 mg, 93%): mp 170−172 °C; H NMR (300
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MHz, DMSO-d6) δ 10.02 (s, 1H), 7.70 – 7.59 (m, 6H), 7.43
13
(t, J = 7.5 Hz, 2H), 7.31 (t, J = 7.2 Hz, 1H), 2.07 (s, 3H); C
{1H} NMR (75 MHz, DMSO-d6) δ 168.3, 139.7, 138.8, 134.6,
128.8, 126.9, 126.8, 126.2, 119.3, 24.0.
2-methoxy-1-phenylnaphthalene (13h).33 The title
compound was prepared as described in the general pro-
cedure using 2-methoxynaphthalene (79.0 mg, 0.5 mmol),
NIS (112.0 mg, 0.5 mmol) and phenylboronic acid (91.5
mg, 0.75 mmol), and purified by using 5 % EtOAc in cy-
1
clohexane as a white solid (111 mg, 95%): H NMR (300
MHz, CDCl3) δ 8.09 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 8.4 Hz,
1H), 7.63 – 7.34 (m, 10H), 2.77 (s, 3H); 13C {1H} NMR (75
MHz, CDCl3) δ 141.1, 138.8, 133.9, 132.9, 131.8, 130.3, 128.9,
128.3, 127.2, 126.8, 126.7, 126.3, 125.7, 124.5, 19.7.
Gram scale reaction. To a stirred solution of anisol 1a
(25 mmol, 2.70 g) in HFIP (30 mL) was added NBS (25
mmol, 4.45 g, 1.0 equiv.) under ice bath. Then remove the
ice bath and the reaction mixture was stirred at rt for 1 h.
After, HFIP solvent was recovered directly by atmospheric
distillation from the reaction pot (27 mL, 90%). The resi-
due was purified under reduced pressure distillation to
afforded 3a as a colorless oil (91%, 4.21 g).
ASSOCIATED CONTENT
Supporting Information
The Supporting Information is available free of charge on the
1
ACS Publications website. Copies of the H and 13C NMR
spectra (PDF).
AUTHOR INFORMATION
Corresponding Author
* E-mail: benoit.crousse@u-psud.fr
Notes
Any additional relevant notes should be placed here.
ACKNOWLEDGMENT
Central Glass Co. Ltd. is greatly appreciated for kindly
providing HFIP. R.-J. T. is grateful for Ph.D. fellowships from
the China Scholarship Council (CSC).
REFERENCES
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