Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[CH2:12]O.C(Br)(Br)(Br)[Br:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[CH2:12][Br:15]Participants
Conditions
- Temperature
- -10 °C
Procedure
To a solution of (2-bromo-5-(trifluoromethyl)phenyl)methanol (4.7 g, 18 mmol) in methylene chloride (50 mL) at −10° C. was added carbon tetrabromide (CBr4) (7.17 g, 21.6 mmol). The resulting mixture was stirred at −10° C. for 15 minutes. Triphenylphosphine (5.61 g, 21.4 mmol) was then slowly added portion-wise. This mixture was stirred at room temperature for 16 hours. The mixture was partitioned between saturated ammonium chloride (NH4Cl) (50 ml) and methylene chloride (2×50 mL). The combined organic layers were washed with saturated NaCl (50 mL), dried (MgSO4) and concentrated. The residue was purified by flash chromatography (silica gel) (eluted with 3:1 hexanes-ethyl acetate) to yield the title compound as a white solid (4.01 g), 1H NMR (400 MHz, CDCl3) δ4.6 (s, 2 H) 7.5 (dd, J=8.3, 1.6 Hz, 1 H) 7.8 (m, 2 H).
Workup
- stirringThis mixture was stirred at room temperature for 16 hours
- customThe mixture was partitioned between saturated ammonium chloride (NH4Cl) (50 ml) and methylene chloride (2×50 mL)
- washThe combined organic layers were washed with saturated NaCl (50 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe residue was purified by flash chromatography (silica gel) (eluted with 3:1 hexanes-ethyl acetate)
Sources & evidence
- ORD record
- ord-ed87383542f840519b50a1653bea9a78
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383660B2
Linked notes
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