3-Fluoro-4-methoxyphenylboronic acid → 8-Fluoro-6-(3-fluoro-4-methoxyphenyl)-2-naphthol

HRID 895230Notes

Reaction equation

HRID 895230 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[CH:8]=[C:7]([OH:13])[CH:6]=[CH:5]2.[F:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]>>[F:12][C:10]1[CH:11]=[C:2]([C:17]2[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:15]([F:14])[CH:16]=2)[CH:3]=[C:4]2[C:9]=1[CH:8]=[C:7]([OH:13])[CH:6]=[CH:5]2

Participants

3

Reactant 2

HCID 27821943-Fluoro-4-methoxyphenylboronic acidHCID 112419396-bromo-8-fluoro-2-naphthol

Product 1

HCID 112084048-Fluoro-6-(3-fluoro-4-methoxyphenyl)-2-naphthol

Procedure

The title compound was prepared by reacting 6-bromo-8-fluoro-2-naphthol (0.66 g, 2.74 mmol) with 3-fluoro-4-methoxyphenyl boronic acid (0.56 g, 3.3 mmol) according to method A to yield 0.67 g (85%) of a white solid: mp 138-140° C.; 1H NMR (DMSO-d6): δ 3.90 (3H, s), 7.17-7.30 (3H, m), 7.60-7.65 (2H, m), 7.71 (1H, dd, J=2.19 Hz), J=13.14 Hz), 7.90 (1H, d, J=8.37 Hz), 7.99 (1H, bs), 10.15 (1H, bs); MS (ESI) m/z285 (M−H)−.

Sources & evidence

ORD record
ord-0b01200112294921b719f0b8d629f1b6
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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