4-Bromobenzoyl chloride → HCID 18434236, compound

HRID 1636733Notes

Reaction equation

HRID 1636733 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[O:23][CH3:24]>[N+](C1C=CC=CC=1)([O-])=O>[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([C:20]2[CH:21]=[C:16]([F:15])[C:17]([O:23][CH3:24])=[CH:18][C:19]=2[F:22])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 685154-Bromobenzoyl chlorideHCID 27249892,5-DifluoroanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18434236HCID 18434236, compound

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Procedure

75 ml of nitrobenzene are cooled in an ice bath and treated in succession with 17.3 g of aluminium chloride and 4-bromobenzoyl chloride in 25 ml of nitrobenzene at a maximum 6° C. The mixture is stirred for 10 min., whereupon 15.7 g of 2,5-difluoroanisole are added in such a manner that the temperature does not exceed 6° C. The solution is left to warm to room temperature overnight, then poured on to ice-water and extracted with methylene chloride. The organic phase is washed with water and 10% sodium chloride solution, dried over sodium sulphate and concentrated. After crystallization from cyclohexane there are obtained 28.4 g of (4-bromo-phenyl)-(2,5-difluoro-4-methoxy-phenyl)-methanone.

Workup

  1. additionare added in such a manner that the temperature
  2. customdoes not exceed 6° C
  3. waitThe solution is left
  4. extractionextracted with methylene chloride
  5. washThe organic phase is washed with water and 10% sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. customAfter crystallization from cyclohexane

Sources & evidence

ORD record
ord-f57087f627b44f859b6124207337375a
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

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