Carbon tetrabromide → HCID 57772011, compound

HRID 1661949Notes

Reaction equation

[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:29][CH3:30])=[CH:20][C:21]([CH2:27]O)=[C:22]([C:23]([F:26])([F:25])[F:24])[C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:51]>C1COCC1>[Br:51][CH2:27][C:21]1[CH:20]=[C:19]([O:29][CH3:30])[C:13]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:10]([C:7]3[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=3)=[N:11][C:12]=2[C:22]=1[C:23]([F:24])([F:26])[F:25]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 655 mg (1.52 mmol) [2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-4-trifluoromethyl-1H-benzoimidazol-5-yl]-methanol in 10 ml THF, 604 mg (2.28 mmol) triphenylphosphine and 764 mg (2.28 mmol) carbon tetrabromide are added at 0° C. The mixture is stirred at 0° C. for 10 min and 30 min at room temperature. Then the reaction mixture is poured on water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=2:1−>1:1) to afford 660 mg of the title compound as a colorless crystalline solid.

Workup

additionThen the reaction mixture is poured on water
extractionextracted (3×) with ethyl acetate
washThe combined organic layers are washed with water (2×) and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=2:1−>1:1)

Sources & evidence

ORD record: ord-2ad145a1a9ef4c4fbfeee8bfe2a080fc
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030497B2

Reaction notes

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