Carbon tetrabromide → 3,5-Difluoro-4-triisopropylsilanyloxybenzyl bromide

HRID 1921875Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[C:4]([F:10])[C:3]=1[O:11][Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14].[Br:22]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:22][CH2:8][C:6]1[CH:5]=[C:4]([F:10])[C:3]([O:11][Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])=[C:2]([F:1])[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

7.40 g (23.4 mmol) of 1,3-difluoro-5-hydroxymethyl-2-triisopropylsilanyloxybenzene are dissolved in 90 ml of dry dichloromethane by stirring at 0° C. under argon. 10.1 g (30.4 mmol) of tetrabromomethane and 7.97 g (30.4 mmol) of triphenylphosphine are successively added to this solution, and the mixture is then stirred under reflux under argon for 12 h. The reaction mixture is washed with water, the organic phase is separated off, dried over magnesium sulfate and filtered, and the solvent is distilled out in vacuo. The oily residue is taken up in diethyl ether and stirred at RT, then filtered, and the filtrate is concentrated. Chromatography of the residue on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 9:1) results in 7.42 g (15.6 mmol, 84% of theory) of the title compound.

Workup

stirringthe mixture is then stirred
temperatureunder reflux under argon for 12 h
washThe reaction mixture is washed with water
customthe organic phase is separated off
dry with materialdried over magnesium sulfate
filtrationfiltered
distillationthe solvent is distilled out in vacuo
stirringstirred at RT
filtrationfiltered
concentrationthe filtrate is concentrated

Sources & evidence

ORD record: ord-2aa110eae3014579aa1cd98e37f48bf7
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173704B2

Reaction notes

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