Hexane → 4-(Bromomethyl)-2-fluorobenzoic acid
Reaction equation
[F:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12]N1C(=O)CCC1=O.CCCCCC>C(Cl)(Cl)(Cl)Cl.C(OCC)(=O)C.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:12][CH2:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([F:1])[CH:10]=1Participants
7
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 2-fluoro-4-methylbenzoic acid (1.029 g, 6.678 mmol) in carbon tetrachloride (10 ml) were added N-bromosuccinimide (1.189 g, 6.682 mmol) and 2,2′-azobisisobutyronitrile (43.9 mg, 0.267 mmol). After stirring at 90° C. for 30 min and at 100° C. for 2.5 hr, the mixture was cooled to 0° C. The precipitate was collected by filtration and washed with hexane and water to give a crude product. The crude product was dissolved in ethyl acetate (5 ml), and hexane (10 ml) was added. The precipitated solid was collected by filtration, and dried under reduced pressure to give 4-(bromomethyl)-2-fluorobenzoic acid (838.6 mg, 3.599 mmol, yield 53.9%) as a slightly yellow solid.
Workup
- temperaturethe mixture was cooled to 0° C
- filtrationThe precipitate was collected by filtration
- washwashed with hexane and water
- customto give a crude product
- filtrationThe precipitated solid was collected by filtration
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-36c165751c56437fbd303adda537f4b5
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507690B2
Reaction notes
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