Boron tribromide → 2-(Bromomethyl)-1-fluoro-4-methylbenzene

HRID 1094449Notes

Reaction equation

B(Br)(Br)[Br:2].[F:5][C:6]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:7]=1[CH2:8]O>>[F:5][C:6]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:7]=1[CH2:8][Br:2]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 12407611(2-Fluoro-5-methylphenyl)methanol

Product 1

HCID 177508002-(Bromomethyl)-1-fluoro-4-methylbenzene

Conditions

Temperature: 7.5 °C

Procedure

An oven dried round bottom flask is charged with boron tribromide (13 mL, 140 mmol) and is cooled to −30-45° C. 2-Fluoro-5-methyl-benzyl alcohol (6.5 g, 46 mmol) is then added slowly after which time the reaction is allowed to warm to room temperature.

Workup

customAn oven dried round bottom flask
temperatureto warm to room temperature

Sources & evidence

ORD record: ord-7bf477cd05cf4987864ad1328f7ce14c
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133907B2

Reaction notes

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