Carbon tetrabromide → (4'-Bromomethyl-3',5'-dichloro-biphenyl-4-yl)-(4-trifluoromethyl-piperidin-1-yl)-methanone

HRID 1692114Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([N:19]3[CH2:24][CH2:23][CH:22]([C:25]([F:28])([F:27])[F:26])[CH2:21][CH2:20]3)=[O:18])=[CH:13][CH:12]=2)[CH:5]=[C:6]([Cl:10])[C:7]=1[CH2:8]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:49]>ClCCl>[Br:49][CH2:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([N:19]3[CH2:24][CH2:23][CH:22]([C:25]([F:28])([F:27])[F:26])[CH2:21][CH2:20]3)=[O:18])=[CH:13][CH:12]=2)=[CH:5][C:6]=1[Cl:10]

Participants

Conditions

Temperature: 0 °C

Procedure

Dissolve (3′,5′-Dichloro-4′-hydroxymethyl-biphenyl-4-yl)-(4-trifluoromethyl-piperidin-1-yl)-methanone (13 g, 1 eq.) in dichloromethane (200 mL) and cool to 0° C. Add triphenylphosphine (12.2 g, 1.5 eq.) followed by carbon tetrabromide (15.4 g, 1.5 eq.) in portions. Filter the reaction mixture and concentrate the filtrate. Chromatograph the filtrate on silica gel to afford 8.0 g (54% yield) of the titled compound.

Workup

filtrationFilter the reaction mixture
concentrationconcentrate the filtrate

Sources & evidence

ORD record: ord-f3739c3307a1407eb211a7ef66952dac
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153807B2

Reaction notes

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