Carbon tetrabromide → 5-Bromo-2-(bromomethyl)-1,3-difluorobenzene

HRID 469829Notes

Reaction equation

HRID 469829 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([F:10])[C:5]([CH2:6]O)=[C:4]([F:11])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>C1COCC1>[Br:1][C:2]1[CH:9]=[C:8]([F:10])[C:5]([CH2:6][Br:32])=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 27733034-Bromo-2,6-difluorobenzyl alcohol

Product 1

HCID 27733055-Bromo-2-(bromomethyl)-1,3-difluorobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 4 g (17.6 mmol) 4-bromo-2,6-difluorobenzyl alcohol in 50 ml THF, 7 g (26.4 mmol) triphenylphosphine and 8.83 g (26.4 mmol) carbon tetrabromide are added with stirring. Stirring is continued for 10 min at 0° C. and for 1 h at room temperature. After that the reaction mixture is filtered and the filtrate is concentrated in vacuo. The residue is purified by chromatography (silicagel, hexane) to afford the title compound as yellowish oil.

Workup

  1. additionare added
  2. stirringStirring
  3. filtrationAfter that the reaction mixture is filtered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customThe residue is purified by chromatography (silicagel, hexane)

Sources & evidence

ORD record
ord-0d02b1b38e944b19896040d89c32db47
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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