[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16]O)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:42]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][Br:42])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19]To a solution of 2-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethanol (300 mg, 0.947 mmol) and triphenylphosphine (300 mg, 1.144 mmol) in dichloromethane (5 mL) was added carbon tetrabromide (350 mg, 1.055 mmol) in portions. The reaction mixture was stirred at rt for 2 h, then concentrated. Purification via ISCO system afforded the title product (335 mg) as a colorless liquid.
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