Benzoyl chloride, 3-bromo- → 6-(3-bromo-benzoyl)-4-methyl-3H-benzoxazol-2-one

HRID 469321Notes

Reaction equation

HRID 469321 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[CH3:11][C:12]1[C:17]2[NH:18][C:19](=[O:21])[O:20][C:16]=2[CH:15]=[CH:14][CH:13]=1.[Cl-].[Cl-].[Cl-].[Al+3]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([C:14]1[CH:13]=[C:12]([CH3:11])[C:17]2[NH:18][C:19](=[O:21])[O:20][C:16]=2[CH:15]=1)=[O:6]

Participants

4

Reactant 3

HCID 74377Benzoyl chloride, 3-bromo-HCID 6451240Aluminum(III) ChlorideHCID 127093364-Methyl-3H-benzooxazol-2-one

Product 1

HCID 581811686-(3-bromo-benzoyl)-4-methyl-3H-benzoxazol-2-one

Procedure

2.08 g (9.48 mmol) 3-bromo-benzoic acid chloride, 1.41 g (9.48 mmol) 4-methyl-3H-benzoxazol-2-one and 5.33 g (40.0 mmol) aluminium trichloride were heated to 125° C. with stirring for 1.5 h. Then the mixture was mixed with ice water and the grease precipitated was separated from the solvent by decanting. The residue was dissolved in EtOAc, evaporated down and a little MeOH was triturated. The precipitate formed was suction filtered, washed with diethyl ether and dried i. vac.

Workup

  1. customthe grease precipitated
  2. customwas separated from the solvent
  3. customby decanting
  4. dissolutionThe residue was dissolved in EtOAc
  5. customevaporated down
  6. customa little MeOH was triturated
  7. customThe precipitate formed
  8. filtrationfiltered
  9. washwashed with diethyl ether
  10. customdried i

Sources & evidence

ORD record
ord-791f12d87530497d82841e3bc08eb5f5
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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