Triethylamine → 7-(Chloromethyl)-5-fluoro-2,3-dihydro-1,4-benzodioxine
Reaction equation
[F:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=[C:4]([CH2:12]O)[CH:3]=1.C(N(CC)CC)C.S(Cl)([Cl:23])=O>ClCCl>[Cl:23][CH2:12][C:4]1[CH:3]=[C:2]([F:1])[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (8-fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)methanol (0.84 g, 4.55 mmol) and triethylamine (960 μl, 4.84 mmol) in dichloromethane (20 mL) was slowly added thionyl chloride (400 μl, 5.47 mmol) at 0° C. The solution was stirred at 0° C. for 15 min then at rt for 3 h. Dichloromethane (80 mL) was added and the solution was washed with water (40 mL), saturated aqueous sodium bicarbonate (40 mL) then brine (40 mL) and dried over sodium sulfate. Filtration and concentration gave 7-(chloromethyl)-5-fluoro-2,3-dihydro-1,4-benzodioxine (0.92 g, quantitative yield) as a brown oil. The chloride was used in the next step without further purification.
Workup
- customat 0° C
- waitat rt for 3 h
- washthe solution was washed with water (40 mL), saturated aqueous sodium bicarbonate (40 mL)
- dry with materialbrine (40 mL) and dried over sodium sulfate
- filtrationFiltration and concentration
Sources & evidence
- ORD record
- ord-a09af8cc166b4f4b96e94c5d17242f8f
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07872014B2
Reaction notes
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