Lithium Bromide → 5-Bromo-2-(bromomethyl)-1,3-difluorobenzene

HRID 1360690Notes

Reaction equation

HRID 1360690 reaction equation
CS(O[CH2:6][C:7]1[C:12]([F:13])=[CH:11][C:10]([Br:14])=[CH:9][C:8]=1[F:15])(=O)=O.[Li+].[Br-:17]>CN(C=O)C.CCOC(C)=O>[Br:14][C:10]1[CH:9]=[C:8]([F:15])[C:7]([CH2:6][Br:17])=[C:12]([F:13])[CH:11]=1

Participants

5

Reactant 2

HCID 82050Lithium BromideHCID 600525854-Bromo-2,6-difluorobenzyl methanesulfonate

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-bromo-2,6-difluorobenzyl methanesulfonate (from Step A above) in DMF (400 mL) was added LiBr (28.8 g, 335 mmol) and heated to 90° C. for 45 minutes. The reaction was cooled to room temperature and diluted with EtOAc. The organic layer was washed with water (5×), brine (2×) dried over MgSO4, and concentrated in vacuo to yield a brown oil. The crude residue was purified via silica gel column chromatography (CH2Cl2/hexanes) to yield the title compound (24 g).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washThe organic layer was washed with water (5×), brine (2×)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto yield a brown oil
  6. customThe crude residue was purified via silica gel column chromatography (CH2Cl2/hexanes)

Sources & evidence

ORD record
ord-c9abc36af02f4f6c88eef7ace38fc923
Source dataset
uspto-grants-2011_02
Patent number
US07879875B2

Reaction notes

Loading…