p-Toluenesulfonic acid → 6-Bromo-2-(4-(trifluoromethyl)phenyl)benzo[d]oxazole

HRID 710109Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[C:4]([OH:21])[CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:9]([C:10]3[CH:11]=[CH:12][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=3)[O:21][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 160 °C

Procedure

Intermediate 53 (940 mg, 2.6 mmol) was dissolved in xylene (25 ml) and added p-Toluenesulphonic acid (991 mg, 5.22 mmol). This mixture was refluxed to 160° C. for 12 h under a dean-stork condenser. Xylene removed from the reaction mixture and basified the residue with aq. NaHCO3 (30 ml). Work up (EtOAc/H2O) followed by purification with combiflash using a gradient mixture of EtOAc and Petether (5:95) as eluent to afford the titled compound (650 mg) as an Off-White solid.

Workup

customXylene removed from the reaction mixture
customfollowed by purification with combiflash
additiona gradient mixture of EtOAc and Petether (5:95) as eluent

Sources & evidence

ORD record: ord-f7efb2f1f2604a2197c24b6e0e15fe8a
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181214B2

Reaction notes

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