Bromide ion → Fosarilate
Reaction equation
[P:1]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])[O:2]CC.[Cl:11][C:12]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br.C(Br)C.[Br-]>>[Cl:11][C:12]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][P:1](=[O:2])([O:5][CH2:6][CH3:7])[O:8][CH2:9][CH3:10]Participants
Conditions
- Temperature
- 158 °C
Procedure
Triethyl phosphite (185 g, 230 ml, 1.1 mole) was placed in a flask equipped with a thermometer, dropping funnel, stirrer and 8 inch Vigreux column with condenser set for downward distillation. The phosphite was heated to 158° C. thereby inducing mild reflux. 6-(2-Chloro-4-methoxyphenoxy)hexyl bromide (320 g, 1 mole) was then added dropwise over a period of 50 minutes. The reaction mixture was heated for an additional 90 minutes at which time distillation of ethyl bromide ceased. The remaining reaction mixture was distilled in vacuo and the fraction (250 g) boiling at 183°-197° C. (0.2-0.3 mm) was collected. The latter was combined with 79 g of product obtained from another run starting from 100 g of bromide and redistilled to give 300 g of diethyl [6-(2-chloro-4-methoxyphenoxy)-hexyl]phosphonate, b.p. 202°-204° C. (0.02 mm).
Workup
- customequipped with a thermometer
- distillation8 inch Vigreux column with condenser set for downward distillation
- customThe remaining reaction mixture
- distillationwas distilled in vacuo
- customthe fraction (250 g) boiling at 183°-197° C. (0.2-0.3 mm) was collected
- customobtained from another run
- distillationredistilled
Sources & evidence
- ORD record
- ord-2a3e2a9b117147dbb705b7b97912f062
- Source dataset
- uspto-grants-1980_01
- Patent number
- US04182759
Reaction notes
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