Boron tribromide → 6-Fluoro-4-hydroxy-biphenyl-3-carboxylic acid 3-nitro-benzylamide

HRID 2229567Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][CH:28]=1)[CH2:7][NH:8][C:9]([C:11]1[CH:12]=[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]([F:19])=[CH:15][C:16]=1[O:17]C)=[O:10])([O-:3])=[O:2].B(Br)(Br)Br>ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][CH:28]=1)[CH2:7][NH:8][C:9]([C:11]1[CH:12]=[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]([F:19])=[CH:15][C:16]=1[OH:17])=[O:10])([O-:3])=[O:2]

Participants

Conditions

Temperature: -78 °C

Procedure

A stirring solution of 6-fluoro-4-methoxy-biphenyl-3-carboxylic acid 3-nitro-benzylamide (2.18 g, 5.7 mmol) in dichloromethane (150 mL, 0.4 M) at −78° C. was treated with BBr3 (27 mL, 27 mmol). The mixture was allowed to stir for 45 min at −78° C. and was then quenched with 100 mL of methanol. The mixture was allowed to warm to room temperature, concentrated, and filtered through a plug of silica gel using 50% ethyl acetate as the eluant. The filtrate was concentrated to provide 6-fluoro-4-hydroxy-biphenyl-3-carboxylic acid 3-nitro-benzylamide (2.1 g, 100%) as a yellow powder: Rf0.68 (50% ethyl acetate in heptane); 1H NMR (CDCl3, 300 MHz) δ 12.29 (bd s, 1H), 8.14-8.09 (m, 2H), 7.65 (d, J=7.2 Hz, 1H), 7.48 (t, J=8.0 Hz, 1H), 7.38-7.29 (m, 5H), 6.74 (d, J=11.4 Hz, 1H), 6.60 (bd s, 1H), 4.68 (d, J=6.0 Hz, 2H).

Workup

customwas then quenched with 100 mL of methanol
temperatureto warm to room temperature
concentrationconcentrated
filtrationfiltered through a plug of silica gel using 50% ethyl acetate as the eluant
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-138ff31cd3454ac392c487318c8d5068
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420426B1

Reaction notes

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