3-Fluoro-4-methoxyphenylboronic acid → HCID 58978545, compound

HRID 1180338Notes

Reaction equation

HRID 1180338 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[CH:6][C:7]=1[CH:8]=[O:9].[F:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:19]([F:18])[CH:20]=2)[CH:5]=[CH:6][C:7]=1[CH:8]=[O:9]

Participants

3

Reactant 2

HCID 27821943-Fluoro-4-methoxyphenylboronic acidHCID 58978534HCID 58978534, compound

Product 1

HCID 58978545HCID 58978545, compound

Procedure

The title compound was prepared by reacting trifluoro-methanesulfonic acid 3-chloro-4-formyl-phenyl ester (2.8 g, 9.62 mmol) with 3-fluoro-4-methoxyphenylboronic acid (1.8 g, 10.6 mmol) according to Method B to yield 1.87 g (74%, over two steps) of white solid: mp 116-118° C.; 1H NMR (DMSO-d6): δ 3.91 (3H, s), 7.30 (1H, t, J=8.79 Hz), 7.66-7.68 (1H, m), 7.79 (1H, dd, J=12.91 Hz, J=2.47 Hz), 7.85-7.87 (1H, m), 7.91 (1H, d, J=8.24 Hz), 7.96 (1H, d, J=1.65 Hz), 10.34 (1H, s); IR 1688 cm−1; MS (ESI) m/z 265/267 (M+H)+.

Workup

  1. customto yield 1.87 g (74%, over two steps) of white solid

Sources & evidence

ORD record
ord-078214afa89d4a1abb4f39491981a6f0
Source dataset
uspto-grants-2007_10
Patent number
US07279600B2

Reaction notes

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