Water → 2-(Bromomethyl)-5-(methylsulphonyl)benzotrifluoride

HRID 1364580Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11]O)=[C:7]([C:13]([F:16])([F:15])[F:14])[CH:6]=1)(=[O:4])=[O:3].P(Br)(Br)[Br:18].O.[OH-].[Na+]>CCOCC>[Br:18][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][C:7]=1[C:13]([F:16])([F:15])[F:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of (4-methanesulfonyl-2-trifluoromethyl-phenyl)-methanol (50.3 g, 0.20 mol) in dry Et2O (400 ml), cooled to 0° C., is added PBr3 (6.5 ml, 0.07 mol) dropwise over 10 min. A sticky, thick yellow suspension forms which upon agitation and warming to room temperature changes to a fine white suspension. The reaction mixture is cooled again to 0° C. and water (200 ml) is added slowly. The suspension is neutralised at 10° C. with 4N NaOH aq (30 ml). The product is collected by filtration to give a white solid which is dried at 50° C. under high vacuum.

Workup

temperatureA sticky, thick yellow suspension forms which upon agitation and warming to room temperature changes to a fine white suspension
temperatureThe reaction mixture is cooled again to 0° C.
filtrationThe product is collected by filtration
customto give a white solid which
customis dried at 50° C. under high vacuum

Sources & evidence

ORD record: ord-a6f0a32350c84ec49454319ce0a0ee4d
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888383B2

Reaction notes

Loading…