Triethylamine → 1-(Chloromethyl)-3-fluoro-2-methoxybenzene
Reaction equation
[F:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([CH2:8]O)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.CS([Cl:23])(=O)=O>ClCCl.C(OCC)C>[Cl:23][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[O:10][CH3:11]Participants
6
Procedure
A solution of (3-fluoro-2-methoxyphenyl)methanol (3.02 g, 19.3 mmol) and triethylamine (6.74 mL, 48.4 mmol) in dichloromethane (20 mL) is treated with methanesulfonyl chloride (2.99 mL, 38.7 mmol) slowly at room temperature and stirred under nitrogen for 3 h. The reaction is the diluted with diethyl ether, washed with 0.5 M hydrochloric acid twice, dried over anhydrous sodium sulfate, filtered, and concentrated to afford the title compound as a yellow oil (2.71 g, 80%). 1H NMR (400 MHz, CDCl3) δ 7.15-6.93 (m, 3H), 4.61 (s, 2H), 4.00 (s, 3H).
Workup
- washwashed with 0.5 M hydrochloric acid twice
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7f0798e1468342ad826ef0fb340b4878
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08486943B2
Reaction notes
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