Water → 6-Bromo-8-methylthiooctanoic acid ethyl ester
Reaction equation
P(Br)(Br)[Br:2].[CH2:5]([O:7][C:8](=[S:18])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13](O)[CH2:14][CH2:15][CH3:16])[CH3:6].O.C(OCC)C>ClC(Cl)(Cl)Cl>[CH2:5]([O:7][C:8](=[S:18])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([Br:2])[CH2:14][CH2:15][CH3:16])[CH3:6]Participants
Conditions
- Temperature
- 0 °C
Procedure
64.8 grams (0.24 mole) of phosphorus tribromide at 0° C. were dropped into a solution of 140.0 grams (0.6 mole) of 6-hydroxy-8-methylthiooctanoic acid ethyl ester (VIb) in 150 ml of tetrachloromethane, the mixture stirred for 2 hours at 0° C. and allowed to stand for 10 hours at room temperature. There were dropped into the reaction mixture, cooled to 0° C., 150 ml of water and subsequently 600 ml of diethyl ether. The organic phase was separated off, washed with saturated aqueous sodium bicarbonate solution, dried with sodium sulfate and the solvent removed in a vacuum. After vacuum distillation of the residue there were obtained 135.0 grams (76% of theory) of 6-bromo-8-methylthiooctanoic acid ethyl ester as a yellowish oil having a boiling point of 140° C. to 145° C. at 1 mbar.
Workup
- waitto stand for 10 hours at room temperature
- additionThere were dropped into the reaction mixture
- temperaturecooled to 0° C.
- customThe organic phase was separated off
- washwashed with saturated aqueous sodium bicarbonate solution
- dry with materialdried with sodium sulfate
- customthe solvent removed in a vacuum
- distillationAfter vacuum distillation of the residue there
Sources & evidence
- ORD record
- ord-999c75df25f54798952d83865e02e0af
- Source dataset
- uspto-grants-1989_01
- Patent number
- US04800044
Reaction notes
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