Carbon tetrabromide → 1-(3-Bromopropyl)-3,5-bis(trifluoromethyl)benzene
Reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH2:13][CH2:14][CH2:15]O)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.CCCCC.C([O-])(O)=O.[Na+]>[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH2:13][CH2:14][CH2:15][Br:20])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
3-[3′,5′-bis(trifluoromethyl)phenyl]-1-propanol (0.88 g, 3.2 mmol) and CBr4 (1.3 g, 4.0 mmol) were dissolved in CH2Cl2 (5 mL) and cooled to 0° C. Triphenylphosphine (1.3 g, 4.8 mmol) was added in three portions over 0.5 h. The mixture was stirred at 0° C. for 10 min., then diluted with pentane (30 mL) and sat. NaHCO3 (30 mL). The aqueous layer was separated and washed with ethyl ether, and the combined organic layers were dried (MgSO4) and concentrated. The residue was purified by silica gel flash chromatography (99:1 ethyl ether-hexane) to yield 0.8 g, (74%) of the 3-[3′,5′-bis(trifluoromethyl)phenyl]-1-bromopropane.
Workup
- customThe aqueous layer was separated
- washwashed with ethyl ether
- dry with materialthe combined organic layers were dried (MgSO4)
- concentrationconcentrated
- customThe residue was purified by silica gel flash chromatography (99:1 ethyl ether-hexane)
Sources & evidence
- ORD record
- ord-21dfaa7b791444258f2b663afb692e36
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278961B2
Reaction notes
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