Methanol → 2-Chloro-1-(4-chloro-2-fluorophenyl)ethan-1-one
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([F:11])[CH:3]=1.CO.S(Cl)([Cl:17])(=O)=O.C(=O)(O)[O-].[Na+]>CCCCCCC>[Cl:17][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[F:11])=[O:10]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
In a 1 L round bottom flask combine 4′-chloro-2′-fluoroacetophenone (40 g, 231.8 mmol), heptane (120 mL), and methanol (16 mL). Cool to 0° C. and place under nitrogen. Dissolve sulfuryl chloride (21.5 mL, 1.15 equiv.) in heptane (120 mL) and charge to an addition funnel Add drop-wise to the reaction over 60 min. Stir for 2.5 h at 0° C.; a white precipitate forms during this time. Charge the addition funnel with 1 M sodium bicarbonate (400 mL) then add to the reaction drop-wise. After all gas evolution stops, filter the biphasic suspension to collect the title compound (38.18 g, 80%) as white needles. 1H NMR (DMSO-d6) δ 5.00 (d, 2H, J=2.5 Hz), 7.43 (m, 1H), 7.63 (m, 1H), 7.89 (t, 1H, J=8.4 Hz).
Workup
- customIn a 1 L round bottom flask combine
- additionAdd
- customdrop-wise to the reaction over 60 min
- additionthen add to the reaction drop-wise
- filtrationfilter the biphasic suspension
- customto collect the title compound (38.18 g, 80%) as white needles
Sources & evidence
- ORD record
- ord-f5f0420a82aa48078fc28410384ae386
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897600B2
Reaction notes
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