Methanol → 4'-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-biphenyl-4-ol

HRID 47658Notes

Reaction equation

B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[N:20]=[C:21]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)[O:22][C:23]=3[CH3:24])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.ClCCl.CO>O>[CH3:24][C:23]1[O:22][C:21]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[N:20][C:19]=1[C:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH:9]=[CH:8][C:7]([OH:6])=[CH:12][CH:11]=2)=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Boron tribromide (1.0 M, 3.91 mL, 3.91 mmol) was added dropwise into a cold (−78° C.) mixture of 4-(4′-methoxy-biphenyl-4-yl)-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazole (1.6 g, 3.91 mmol), and dichloromethane (20 mL). The reaction mixture was allowed to come gradually to room temperature and stirred for 10 hours. Then, the mixture was cooled to 0° C. and methyl alcohol (5 mL) was added dropwise. After stirring for 10 minutes the mixture was poured into water and extracted with ethyl ether. The organic extracts were dried over MgSO4. Evaporation and crystallization from ethyl ether/hexanes gave an off-white solid (1.4 g, 90% yield): mp 189-191; MS m/e 396 (M+H)+;

Workup

customto come gradually to room temperature
stirringAfter stirring for 10 minutes the mixture
extractionextracted with ethyl ether
dry with materialThe organic extracts were dried over MgSO4
customEvaporation and crystallization from ethyl ether/hexanes

Sources & evidence

ORD record: ord-e8083fdac2af467aa85d1f0558d396c6
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699896B1

Reaction notes

Loading…