Water → 1-(Chloromethyl)-2-fluoro-3-methoxybenzene
Reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:10]O.P(Cl)(Cl)(Cl)(Cl)[Cl:13].O>C(Cl)(Cl)(Cl)Cl>[Cl:13][CH2:10][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([O:8][CH3:9])[C:2]=1[F:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of (2-fluoro-3-methoxyphenyl)methanol (13 g, 83.2 mmol) in CCl4 (75 mL), PCl5 (26 g, 128.7 mmol) was added. The resulting mixture was heated at 90° C. for 30 min and then stirred at room temperature for 1 h. The mixture was poured into water (160 mL) and extracted with dichloromethane (2×150 mL). The combined organic layers were washed with brine (200 mL), dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel column chromatography (1:15 EtOAc/petroleum ether) to give the title compound (11.5 g). 1H NMR (CDCl3): δ 7.10-6.91 (m, 3H), 4.63 (s, 2H), 3.89 (s, 3H).
Workup
- extractionextracted with dichloromethane (2×150 mL)
- washThe combined organic layers were washed with brine (200 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography (1:15 EtOAc/petroleum ether)
Sources & evidence
- ORD record
- ord-65943c9f560944cab3a2afcfd0c2d196
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09078871B2
Reaction notes
Loading…