Dichloromethane → 3-(4-Bromophenyl)propyl methanesulphonate

HRID 217784

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.ClCCl.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(N(CC)CC)C>[CH3:15][S:16]([O:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)(=[O:18])=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

3-(4-Bromophenyl)propan-1-ol (335 g) and dichloromethane (2.5 L) was charged into Reactor 1. Reactor 1 was adjusted to −10 to 0° C. Triethylamine (205 g) was charged into Reactor 1. Methanesulphonyl chloride (272.7 g) was added dropwise into Reactor 1 maintaining contents at <0° C. Reactor 1 was stirred at −5 to 5° C. for 1 h then analysed for reaction completion. The organic layer was washed with water (1 L) and saturated NaCl solution (1 L). The organic layer was evaporated down to dryness to give 3-(4-bromophenyl)propyl methanesulfonate (418 g).

Workup

customReactor 1 was adjusted to −10 to 0° C
customthen analysed for reaction completion
washThe organic layer was washed with water (1 L) and saturated NaCl solution (1 L)
customThe organic layer was evaporated down to dryness

Sources & evidence

ORD record: ord-7e3f71f2fd514fcd9d7d6fb40e69d52f
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198285B2

Linked notes

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