Thionyl Chloride → 4-{4-[(4-Bromobutyl)oxy]butyl}benzoyl chloride
Reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=1.S(Cl)([Cl:22])=O>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([Cl:22])=[O:16])=[CH:13][CH:12]=1Participants
3
Procedure
A suspension of 4-{4-[(4-bromobutyl)oxy]butyl}benzoic acid (0.91 g, 2.77 mmol, e.g. which can be as prepared in Intermediate 25) in thionyl chloride (SOCl2, 2 ml) was stirred at room temperature for 1 hour and then at 100° C. for 2 hours. The reaction mixture was cooled and the excess thionyl chloride was removed by evaporation, followed by co-evaporation with dichloromethane (2×30 ml) to give the title compound as a brown oil (1.03 g). 1H NMR (400 MHz, chloroform-d) δ (delta) ppm 1.5-2.0 (10H, m); 2.75 (2H, m); 3.45 (4H, m); 7.35 (2H, d); 8.05 (2H, d). The compound was not pure by 1H NMR (CDCl3), but it was not purified further.
Workup
- waitat 100° C. for 2 hours
- temperatureThe reaction mixture was cooled
- customthe excess thionyl chloride was removed by evaporation
Sources & evidence
- ORD record
- ord-335699b7010d440abb4941718a3c366e
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003663B2
Reaction notes
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