Boron tribromide → HCID 59485749, compound

HRID 1972206Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C@@H:13]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)[CH2:12][O:11][C:10]2=[O:24])=[CH:5][CH:4]=1.FC(F)(F)C1C=C([C@H]2COC(=O)N2)C=CC=1.IC1C=CC(OC)=CC=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C@@H:13]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)[CH2:12][O:11][C:10]2=[O:24])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (S)-3-(4-methoxy-phenyl)-4-(3-trifluoromethyl-phenyl)-oxazolidin-2-one (57 mg, 0.169 mmol, prepared from (S)-4-(3-trifluoromethyl-phenyl)-oxazolidin-2-one and 1-iodo-4-methoxy-benzene using the same condition as example 4) in CH2Cl2 (1 mL) is cooled down to −78° C. in a dry ice bath when BBr3 (0.371 mmol, 1M in CH2Cl2) is added into the mixture dropwise. After the addition, the mixture is allowed to warm up to 0° C. and stirred for 1 h. The reaction is then quenched at 0° C. by adding MeOH (0.5 mL) and diluted with water (2 mL). After extraction with CH2Cl2 (3×2 mL), the combined organic layers were concentrated and purified by a flash column chromatography (silica gel, EtOAc/hexane 0˜50%) to provide the desired (S)-3-(4-hydroxy-phenyl)-4-(3-trifluoromethyl-phenyl)-oxazolidin-2-one (47 mg, 86%). HPLC-MS calculated for C16H12F3NO3 (M+H+) 324.1, found 324.1.

Workup

additionis added into the mixture dropwise
additionAfter the addition
customThe reaction is then quenched at 0° C.
additionby adding MeOH (0.5 mL)
additiondiluted with water (2 mL)
extractionAfter extraction with CH2Cl2 (3×2 mL)
concentrationthe combined organic layers were concentrated
custompurified by a flash column chromatography (silica gel, EtOAc/hexane 0˜50%)

Sources & evidence

ORD record: ord-c17b3e9de7024f2eaac1cd4804510c02
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431607B2

Reaction notes

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