Carbon tetrabromide → 5-(Bromomethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole

HRID 460015

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[S:5][C:6]=1[CH2:7]O.C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl.C1CCCCC1>[Br:20][CH2:7][C:6]1[S:5][C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[N:3][C:2]=1[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of {4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methanol (intermediate 1, 0.9 g) in dry dichloromethane (30 ml) stirring at 0° C. was added carbon tetrabromide (1.1 g) and triphenylphosphine (0.995 g). The reaction was stirred at 0° C. for 1 hour, diluted with cyclohexane (30 ml) and purified by SPE cartridge (Si cartridge using chloroform:cyclohexane (1:1) to give the title compound as a white solid.

Workup

custompurified by SPE cartridge (Si cartridge

Sources & evidence

ORD record: ord-462655ef133b43e0badbf023b32817be
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196107B2

Linked notes

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