Dimethylformamide → 1-Bromo-2-(chloromethyl)-3-fluorobenzene

HRID 889144Notes

Reaction equation

HRID 889144 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9]O.CN(C)C=O.[OH-].[Na+].S(Cl)([Cl:20])=O>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][Cl:20]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 44181801(2-Bromo-6-fluorophenyl)methanol

Product 1

HCID 547587241-Bromo-2-(chloromethyl)-3-fluorobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

After dissolving (2-bromo-6-fluorophenyl)methanol (CAS 261723-33-5) (4.07 g) in toluene (50 ml), thionyl chloride (2.21 ml) was added dropwise while stirring on ice. N,N-Dimethylformamide (0.1 ml) was then added and the mixture was stirred for 6 hours. The reaction mixture was diluted with water, a 1N aqueous solution of sodium hydroxide was added and extraction was performed with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure to obtain the title compound (4.45 g).

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred for 6 hours
  3. extractionextraction
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4b66c80d7b7b4579a674d034a7875193
Source dataset
uspto-grants-2012_08
Patent number
US08252810B2

Reaction notes

Loading…