Dichloromethane → 2-(1-Bromoethyl)-3-chloro-1,4-difluorobenzene

HRID 659314Notes

Reaction equation

HRID 659314 reaction equation
P(Br)(Br)[Br:2].C(Cl)Cl.[Cl:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]([F:16])[C:10]=1[CH:17](O)[CH3:18]>O>[Br:2][CH:17]([C:10]1[C:9]([Cl:8])=[C:14]([F:15])[CH:13]=[CH:12][C:11]=1[F:16])[CH3:18]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 24614Phosphorus tribromideHCID 211113742-Chloro-3,6-difluoro-α-methylbenzenemethanol

Product 1

HCID 578860042-(1-Bromoethyl)-3-chloro-1,4-difluorobenzeneYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphorus tribromide (1.3 mL) and anhydrous CH2Cl2 (50 mL) were combined and then cooled over ice water for 20 minutes. The cooled solution was then added to a mixture of 1-(2-chloro-3,6-difluorophenyl)ethanol (2.71 g) and methylene chloride (50 mL), and the resulting mixture was stirred at room temperature for two (2) hours. The mixture was then poured into H2O and extracted into CH2Cl2. The organic phase was isolated, dried with magnesium sulfate, filtered, and concentrated to give the title compound (78% yield).

Workup

  1. extractionextracted into CH2Cl2
  2. customThe organic phase was isolated
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-927ec4335dd24913b359c537d8314ebb
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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