Methanesulfonyl chloride → HCID 53997182, compound

HRID 1455959Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH:16]([OH:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:19](Cl)([CH3:22])(=[O:21])=[O:20]>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:22][S:19]([O:18][CH:16]([C:10]1[CH:11]=[C:12]([Br:15])[CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:17])(=[O:21])=[O:20]

Participants

Conditions

Temperature: -10 °C

Procedure

1-(2-Benzyloxy-5-bromophenyl)-ethanol (3.74 g) was dissolved in pyridine (15 mL) and cooled to -10° C. under argon. Mesyl chloride (0.95 mL) was added dropwise over ten minutes and the mixture stirred allowing to come to ambient temperature over seventeen hours. The mixture was diluted with ethyl acetate (100 mL) and then washed with hydrochloric acid (1M, 3×70 mL) until the organic phase tested to pH 1. The ethyl acetate fraction was then washed with saturated sodium hydrogen carbonate solution (50 mL) and dried (MgSO4). After removal of solvent the oily residue was purified by MPLC (eluting 75% dichloromethane, 25% hexane, silica) to give 1-(2-benzyloxy-5-bromophenyl)ethanol methanesulphonate which was used rapidly without further purification, yield 1.19 g.

Workup

waitto come to ambient temperature over seventeen hours
washwashed with hydrochloric acid (1M, 3×70 mL) until the organic phase
washThe ethyl acetate fraction was then washed with saturated sodium hydrogen carbonate solution (50 mL)
dry with materialdried (MgSO4)
customAfter removal of solvent the oily residue
customwas purified by MPLC (eluting 75% dichloromethane, 25% hexane, silica)

Sources & evidence

ORD record: ord-e2e0f5128407441c9aef0ebdc896005f
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05843942

Reaction notes

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