Hydrochloric Acid → N-[4-(2-bromo-1-hydroxyethyl)phenyl]methanesulfonamide

HRID 373156Notes

Reaction equation

[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][CH:6]=1)=[O:4].[BH4-].[Na+].Cl.O>CO.C(Cl)(Cl)Cl>[Br:1][CH2:2][CH:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:9][CH:10]=1)[OH:4]

Participants

Conditions

Temperature: -20 °C

Procedure

20.0 g (61.0 mmol) of N-[4-(2-bromoacetyl)phenyl]methanesulfonamide was suspended in 240 ml of methanol. 2.84 g of sodium borohydride was added in three portions at intervals of 5 min to the suspension cooled at -20° C. The mixture was stirred at -20° C. for 2 h. Concentrated hydrochloric acid was added dropwise to the mixture to acidify it. 300 ml of water and 500 ml of chloroform were added thereto. After extraction with chloroform, the organic layer was concentrated and a solid residue thus obtained was recrystallized from ether to give 16.4 g (yield: 82%) of the intended compound in the form of white crystals.

Workup

extractionAfter extraction with chloroform
concentrationthe organic layer was concentrated
customa solid residue thus obtained
customwas recrystallized from ether

Sources & evidence

ORD record: ord-cd3d39f3a2d54c6487344bd7559811c7
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05162347

Reaction notes

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