Triphenylphosphine → 1-Bromo-3-(bromomethyl)-5-fluorobenzene
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9]O)[CH:5]=[C:6]([F:8])[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:30]N1C(=O)CCC1=O>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH2:9][Br:30])[CH:3]=1Participants
6
Conditions
- Temperature
- 0 °C
Procedure
(3-Bromo-5-fluorophenyl)methanol (0.78 g, 3.8 mmol) and triphenylphosphine (2.0 g, 7.6 mmol) were combined in tetrahydrofuran (20 mL) and cooled to 0° C. N-Bromosuccinimide (1.4 g, 7.98 mmol) was introduced in portions and the reaction allowed to warm to room temperature. After 16 h, the reaction mixture was diluted with ethyl acetate, washed with concentrated sodium bicarbonate (2×), then brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (5% ethyl acetate/hexanes) gave 0.8 g (79%) as a white powder. 1H-NMR (CDCl3, 300 MHz) 7.30 (s, 1H), 7.14-7.18 (m, 1H), 7.01-7.05 (m, 1H), 4.36 (s, 2H).
Workup
- temperatureto warm to room temperature
- washwashed with concentrated sodium bicarbonate (2×)
- dry with materialbrine (2×), dried over sodium sulfate
- concentrationconcentrated
- customColumn chromatography on silica gel (5% ethyl acetate/hexanes) gave 0.8 g (79%) as a white powder
Sources & evidence
- ORD record
- ord-8a62d4564f754f1bb09e3eea00d06bd6
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383821B2
Reaction notes
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