Water → 2-Bromo-1-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethanol

HRID 1445769Notes

Reaction equation

HRID 1445769 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][C:18]([CH3:23])=[C:19]([CH:21]=[CH2:22])[N:20]=2)=[CH:12][CH:11]=1.CCOC(C)=O.[OH2:30]>CS(C)=O>[Br:8][CH2:22][CH:21]([C:19]1[N:20]=[C:16]([C:13]2[CH:12]=[CH:11][C:10]([Br:9])=[CH:15][CH:14]=2)[O:17][C:18]=1[CH3:23])[OH:30]

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 222611552-(4-Bromo-phenyl)-5-methyl-4-vinyl-oxazole

Product 1

HCID 589514762-Bromo-1-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethanolYield 74%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Add NBS (1.44 g, 8.08 mmol) to a solution of 2-(4-bromo-phenyl)-5-methyl-4-vinyl-oxazole (1.01 g, 4.02 mmol) in water (0.180 mL) and DMSO (30 mL). After 10 min add water and EtOAc. Separate the layers, extract aqueous material with EtOAc, and wash the crude organic extracts with water. Dry over MgSO4, filter and concentrate. Purify on silica gel eluting with 20% EtOAc/Hexanes to give the title compound (1.08 g, 74%): MS (m/e): 362 (M+1).

Workup

  1. customSeparate the layers
  2. extractionextract aqueous material with EtOAc
  3. washwash the crude organic extracts with water
  4. dry with materialDry over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify on silica gel eluting with 20% EtOAc/Hexanes

Sources & evidence

ORD record
ord-8491e4d3783b47c2be8d86ebb8dcafdb
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

Loading…