Sodium Carbonate → 1-Bromo-4-(bromomethyl)-2-fluorobenzene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][C:3]=1[F:10].P(Br)(Br)[Br:12].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:12])=[CH:4][C:3]=1[F:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a solution of (4-bromo-3-fluorophenyl)methanol (5 g, 24.39 mmol) in DCM (100 mL) was added PBr3 (2.76 mL, 29.3 mmol) dropwise. The resulting mixture was stirred at 20° C. After LCMS analysis showed the starting material had disappeared, the mixture was adjusted to pH=8 by aq Na2CO3. The organic layer was dried and concentrated to give the crude product, which was purified by column chromatography (PE/EA=10/1) to yield a white solid of 1-bromo-4-(bromomethyl)-2-fluorobenzene (4.2 g, 14.89 mmol, 61.1% yield): 1H NMR (400 MHz, CD3OD) δ 7.57 (d, J=7.6 Hz, 1H), 7.28 (d, J=7.2 Hz, 1H), 7.16 (d, J=6.4 Hz, 1H), 4.53 (s, 2H); ES-LCMS m/z 186.9 (M−79).
Workup
- customThe organic layer was dried
- concentrationconcentrated
- customto give the crude product, which
- customwas purified by column chromatography (PE/EA=10/1)
Sources & evidence
- ORD record
- ord-46e44217c6004e949fbd39aff2308958
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937071B2
Reaction notes
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