Hydrogen Bromide → 2-Bromo-1-(2-phenyl-benzoxazol-6-yl)-butan-1-one

HRID 1619958Notes

Reaction equation

HRID 1619958 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[C:14]([C:16](=[O:20])[CH2:17][CH2:18][CH3:19])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-:21].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.Br.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O>[Br:21][CH:17]([CH2:18][CH3:19])[C:16]([C:14]1[CH:13]=[CH:12][C:10]2[N:11]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:8][C:9]=2[CH:15]=1)=[O:20]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 21124087PyridiniumtribromideHCID 674660111-(2-Phenyl-benzoxazol-6-yl)butan-1-one

Product 1

HCID 866890652-Bromo-1-(2-phenyl-benzoxazol-6-yl)-butan-1-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

400 mg (1.51 mmol) 1-(2-phenyl-benzoxazol-6-yl)-butan-1-one and 643 mg (1.81 mmol) pyridinium tribromide are dissolved in 4 ml glacial acetic acid at RT, then 1.04 ml (5.40 mmol) hydrogen bromide, dissolved 30% in glacial acetic acid, are added and the mixture is stirred for 1 h at RT. Then the reaction mixture is mixed with water and adjusted to pH 8 with 5% potassium carbonate solution, then it is extracted with DCM, the org. phase is dried on magnesium sulphate and the solv. is eliminated completely in vacuo. The residue is separated through silica gel (eluant cyclohexane/EA).

Workup

  1. additionare added
  2. extractionit is extracted with DCM
  3. customphase is dried on magnesium sulphate
  4. customThe residue is separated through silica gel (eluant cyclohexane/EA)

Sources & evidence

ORD record
ord-2aff2ccdaab2469fa39985af4e4f2357
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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