Thionyl Chloride → 1-(Chloromethyl)-4-fluoro-2-methylbenzene
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[C:4]([CH3:10])[CH:3]=1.O=S(Cl)[Cl:13]>C(Cl)Cl>[Cl:13][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[CH3:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
(4-Fluoro-2-methylphenyl)methanol (11.5 g, 82 mmol) was dissolved in CH2Cl2 (100 mL). The mixture was cooled to 0° C. before adding SOCl2 (10.7 g, 90 mmol), then stirred for 30 min at 0° C. and then at room temperature for 1.5 h. The solvent and excess of SOCl2 were removed by evaporation followed by the addition of CH2Cl2. The solvent and remaining traces of SOCl2 were evaporated once more. There was obtained 13.0 g (100%) of 1-(chloromethyl)-4-fluoro-2-methylbenzene as an oil. 1H NMR (300 MHz, CDCl3): 2.4 (s, 3H), 4.6 (s, 2H), 6.8-7.0 (m, 2H), 7.3 (m, 1H).
Workup
- waitat room temperature for 1.5 h
- customThe solvent and excess of SOCl2 were removed by evaporation
- additionfollowed by the addition of CH2Cl2
- customwere evaporated once more
Sources & evidence
- ORD record
- ord-e4780ea8b04548c3aacbdfe22a6d5b38
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07402581B2
Reaction notes
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