[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH2:10][CH:11]([CH2:13]O)[N:12]=2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35]>N1C=CC=CC=1>[Br:35][CH2:13][CH:11]1[CH2:10][O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:12]1To a solution of [2-(4-fluorophenyl)-1,3-oxazolin-4-yl]methan-1-ol (500 mg, 2.5 mmol) in pyridine (30 ml) cooled to 0° under inert conditions was added triphenylphosphine (1.3 g, 5.0 mmol). Carbon tetrabromide (817 mg, 2.5 mmol) was added in 4 fractions (˜200 mg each). The reaction mixture was stirred at zero degrees until all starting material was consumed, as shown by TLC (1:1 EtOAc:Hexanes). Methanol (˜5 ml) was added to quench the reaction. The solution was evaporated under reduced pressure, and the residue was purified using column chromatography (1:1 EtOAc:Hexanes) to yield compound 4-(bromomethyl)-2-(4-fluorophenyl)-1,3-oxazoline (300 mg, HNMR).
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