Carbon tetrabromide → 4-(2-Bromoethyl)-1,2-bis(difluoromethoxy)benzene
Reaction equation
[F:1][CH:2]([F:17])[O:3][C:4]1[CH:5]=[C:6]([CH2:14][CH2:15]O)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:38]>ClCCl>[Br:38][CH2:15][CH2:14][C:6]1[CH:7]=[CH:8][C:9]([O:10][CH:11]([F:13])[F:12])=[C:4]([O:3][CH:2]([F:17])[F:1])[CH:5]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
2-[3,4-Bis(difluoromethoxy)phenyl]ethanol (6 g, 0.024 mol; see step (iv) above) and triphenylphosphine (12.6 g, 0.048 mol) were taken up in dichloromethane (100 mL) and cooled to 0° C. CBr4 (15.9 g, 0.048 mol) in dichloromethane was added dropwise, and the mixture stirred at RT overnight under a nitrogen atmosphere. The reaction mixture was filtered, the filtrate concentrated under reduced pressure and the residue purified by column chromatography over silica gel (using 20% ethyl acetate in petroleum ether as eluent) to give the title compound as a yellow liquid. Yield 5.2 g.
Workup
- filtrationThe reaction mixture was filtered
- concentrationthe filtrate concentrated under reduced pressure
- customthe residue purified by column chromatography over silica gel (using 20% ethyl acetate in petroleum ether as eluent)
Sources & evidence
- ORD record
- ord-133c460592124f9088fe2022a88bcc45
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07648985B2
Reaction notes
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