3-Bromo-4-fluorobenzoyl chloride → 6-(3-bromo-4-fluoro-benzoyl)-4-methyl-3H-benzoxazol-2-one

HRID 469333Notes

Reaction equation

HRID 469333 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5](Cl)=[O:6].[CH3:12][C:13]1[C:18]2[NH:19][C:20](=[O:22])[O:21][C:17]=2[CH:16]=[CH:15][CH:14]=1.[Cl-].[Cl-].[Cl-].[Al+3]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([C:15]1[CH:14]=[C:13]([CH3:12])[C:18]2[NH:19][C:20](=[O:22])[O:21][C:17]=2[CH:16]=1)=[O:6]

Participants

4

Reactant 3

HCID 695983-Bromo-4-fluorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 127093364-Methyl-3H-benzooxazol-2-one

Product 1

HCID 581811656-(3-bromo-4-fluoro-benzoyl)-4-methyl-3H-benzoxazol-2-one

Procedure

2.23 g (9.40 mmol) 3-bromo-4-fluoro-benzoic acid chloride, 1.40 g (9.40 mmol) 4-methyl-3H-benzoxazol-2-one and 5.01 g (37.60 mmol) aluminium trichloride were heated to 125° C. for 1.5 h with stirring. After cooling to RT the mixture was mixed with ice water. The precipitate formed was suction filtered and washed with water. Then the precipitate was triturated with MeOH, suction filtered, washed with MeOH and dried i. vac.

Workup

  1. customThe precipitate formed
  2. filtrationfiltered
  3. washwashed with water
  4. customThen the precipitate was triturated with MeOH, suction
  5. filtrationfiltered
  6. washwashed with MeOH
  7. customdried i

Sources & evidence

ORD record
ord-f0500187676c41158cfad604f0265059
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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