Boron tribromide → Ethyl (4-{[(6-chloro-2-fluoro-3-hydroxyphenyl)carbonyl]amino}phenyl)acetate

HRID 1879121Notes

Reaction equation

B(Br)(Br)Br.[CH2:5]([O:7][C:8](=[O:29])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:19]2[C:24]([Cl:25])=[CH:23][CH:22]=[C:21]([O:26]C)[C:20]=2[F:28])=[O:18])=[CH:12][CH:11]=1)[CH3:6]>ClCCl>[Cl:25][C:24]1[C:19]([C:17]([NH:16][C:13]2[CH:12]=[CH:11][C:10]([CH2:9][C:8]([O:7][CH2:5][CH3:6])=[O:29])=[CH:15][CH:14]=2)=[O:18])=[C:20]([F:28])[C:21]([OH:26])=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Boron tribromide (393 μl, 4.16 mmol) was added dropwise to a solution of ethyl[4-({[6-chloro-2-fluoro-3-(methyloxy)phenyl]carbonyl}amino)phenyl]acetate (506 mg, 1.39 mmol) in dichloromethane (30 ml) at −78° C. under argon and the reaction was stirred overnight whilst slowly warming to 0° C. The reaction was quenched by the careful addition of water, stirred for 1 hour, further diluted with ethyl acetate, filtered, phases separated, the organic layer dried (Na2SO4) and solvent evaporated and the residue purified by flash chromatography (Biotage SP4, 25+M silica column, 0→80% ethyl acetate/petrol, clean fractions collected) to afford the title compound as a colourless foam (157 mg, 32%).

Workup

customThe reaction was quenched by the careful addition of water
stirringstirred for 1 hour
additionfurther diluted with ethyl acetate
filtrationfiltered
customphases separated
dry with materialthe organic layer dried (Na2SO4) and solvent
customevaporated
customthe residue purified by flash chromatography (Biotage SP4, 25+M silica column, 0→80% ethyl acetate/petrol, clean fractions collected)

Sources & evidence

ORD record: ord-a2a63743711c4534a499535c8a10ca59
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314147B2

Reaction notes

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