Carbon tetrabromide → 4-(Bromomethyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazole

HRID 1689803Notes

Reaction equation

[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=3[Cl:16])[C:5]=2[CH2:17]O)[CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:39]>ClCCl>[Br:39][CH2:17][C:5]1[C:6]([C:9]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:16])=[N:7][O:8][C:4]=1[CH:1]1[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 30 g (105.58 mmol) of [5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-yl]-methanol in 210 mL of dichloromethane is added 41.96 g (158 mmol) of triphenylphosphine. The resulting mixture is cooled in an ice bath (about 0-10° C.) and added in portions to carbon tetrabromide (53 g, 158.37 mmol). The reaction is stirred at room temperature for 2 h. The solvent is evaporated to obtain an orange oil which is purified on silica gel column chromatography using Hexanes to hex/EtOAc 8:2 as eluent, to obtain 33 g of the title compound as a white solid (90%). MS (m/e): 346 (M+1).

Workup

customThe solvent is evaporated
customto obtain an orange oil which
customis purified on silica gel column chromatography

Sources & evidence

ORD record: ord-81eeab1577af4cb79733fa3b58a8b02e
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153624B2

Reaction notes

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