Carbon tetrabromide → 5-(bromomethyl)-2,2-difluorobenzo[d][1,3]dioxole
Reaction equation
[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11]O)=[CH:10][C:4]=2[O:3]1.C(Br)(Br)(Br)[Br:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:15][CH2:11][C:9]1[CH:8]=[CH:7][C:5]2[O:6][C:2]([F:13])([F:1])[O:3][C:4]=2[CH:10]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (2,2-difluorobenzo[d][1,3]dioxol-5-yl)methanol (120 mg; 0.63 mmol) in anh. DCM (5 ml) was treated at rt with CBr4 (211 mg; 0.63 mmol), and with PPh3 (167 mg; 0.63 mmol). The resulting mixture was further stirred at rt, under nitrogen, for 17 h. Concentration to dryness under reduced pressure, and subsequent purification by FC (DCM) afforded 5-(bromomethyl)-2,2-difluorobenzo[d][1,3]dioxole as a pale yellow oil which was directly used for the next reaction.