N-bromobutanimide → 2-(Bromomethyl)-5-(2'-methoxy-5'-fluorophenethyl)tetrahydrofuran
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[CH2:10][CH2:11][CH:12]([OH:17])[CH2:13][CH:14]=[CH:15][CH3:16].[Br:18]N1C(=O)CCC1=O>C(Cl)Cl>[Br:18][CH2:16][CH:15]1[CH2:14][CH2:13][CH:12]([CH2:11][CH2:10][C:4]2[CH:5]=[C:6]([F:9])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[O:17]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-(2′-methoxy-5′-fluorophenyl)hept-5-en-3-ol (3.5 g, 14.7 mmol) in dry CH2Cl2 (90 mL) at 0° C. was added N-bromosuccinimide (NBS, 3.15 g, 17.0 mmol) portionwise and the reaction was warmed to room temperature for 12 h. Solvent was then removed in vacuo and the residue was purified by flash column chromatography (5% EtOAc in Hexane, Rf=0.12) to result in the trans isomer (2.05 g, 44%) as an oil; and the cis isomer (743 mg, 16%) as an oil; and mixture of both isomers (1.35 g, 29%).