Boron tribromide → 1-(5-chloro-2-hydroxy-4-methyl-3-nitrophenyl)ethanone

HRID 510825Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH3:16])=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([O:11]C)=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:3]([CH3:16])=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a mixture of 1-(5-chloro-2-methoxy-4-methyl-3-nitrophenyl)ethanone (8.9 g, 37 mmol, from Oakwood) in methylene chloride (200 mL) was added 1.0 M boron tribromide in methylene chloride (38.4 mL, 38.4 mmol) at −78° C. After stirring at −78° C. for 10 minutes, the reaction was allowed to warm up to 0° C., quenched with water at 0° C., and extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and filtered. After evaporating to dryness under reduced pressure, the residue was used directly in next step (8.2 g, 98%). LCMS calculated for C9H9ClNO4 (M+H)+: m/z=230.0. found: 230.1.

Workup

temperatureto warm up to 0° C.
customquenched with water at 0° C.
extractionextracted with dichloromethane
washThe combined organic layers were washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
customAfter evaporating to dryness under reduced pressure

Sources & evidence

ORD record: ord-fbfaa6712b7c473e897042a074ae24ed
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096600B2

Reaction notes

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