Methanol → 3,4'-Difluoro-5-hydroxystilbene

HRID 78883Notes

Reaction equation

B(Br)(Br)Br.C([O:12][C:13]1[CH:14]=[C:15]([F:28])[CH:16]=[C:17]([CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH:18]=1)C1C=CC=CC=1.CO>C(Cl)Cl>[F:28][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH:18]=[C:13]([OH:12])[CH:14]=1

Participants

Conditions

Temperature: -20 °C

Procedure

A 1 M solution of BBr3 (9 ml, 9 mmol) in CH2Cl2 was added to a well-stirred solution of 5-benzyloxy-3,4′-difluorostilbene (0.97 g, 3 mmol) in dry CH2Cl2 (120 ml) at −78° C. The mixture was warmed to −20° C. and stirred for 10 minutes. Then MeOH was added at −78° C. The mixture was washed with saturated NaHCO3, and water. Flash chromatography gave the 3,4′-difluoro-5-hydroxystilbene (0.60 g, 86%) as white solid. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.46 (m, 2H), 7.08-6.73 (m, 6H), 6.48 (dt, 1H), 4.85 (s, 1H); 13C NMR (CDCl3, 75 MHz) δ 165.05 (d), 161.78 (d), 157.06 (d), 140.43 (d), 133.06 (d), 129.40 (s), 128.45 (d), 127.25 (t), 115.95 (d), 109.42 (d), 105.91 (d), 102.60 (d); 19F NMR (CDCl3, 282 MHz) δ −31703.17 (t), −32099.92 (t); HRMS (EI+) found 232.0714 M+, calcd 232.0700 for C14H10F2O.

Workup

washThe mixture was washed with saturated NaHCO3, and water

Sources & evidence

ORD record: ord-3cac20b1b97646bc9ac48cb2b2a9dba0
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841477B2

Reaction notes

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