1,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene → 2-(4-bromo-3-methyl-phenyl)-4-(3,5-dichloro-phenyl)-4-trifluoromethyl-3,4-dihydro-2H-pyrrole

HRID 1505269Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]([F:13])([F:12])[F:11])=[CH2:9])[CH:5]=[C:4]([Cl:14])[CH:3]=1.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N+:23]#[C-:24])=[CH:18][C:17]=1[CH3:25]>C1(C)C=CC=CC=1.[Cu-]=O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:9][C:8]([C:6]3[CH:5]=[C:4]([Cl:14])[CH:3]=[C:2]([Cl:1])[CH:7]=3)([C:10]([F:11])([F:13])[F:12])[CH:24]=[N:23]2)=[CH:18][C:17]=1[CH3:25]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene (preparation described in, for example, EP 1,731,512) (8.03 g), 1-bromo-4-isocyanomethyl-2-methyl-benzene (Example 10.3) (4.16 g) and copper(I) oxide (0.13 g) in toluene (50 ml) was stirred at 110° C. for 16 hours. The reaction mixture was concentrated and the residue purified by chromatography on silica gel (eluent: ethyl acetate/heptane) to give 2-(4-bromo-3-methyl-phenyl)-4-(3,5-dichloro-phenyl)-4-trifluoromethyl-3,4-dihydro-2H-pyrrole (2.39 g). 1H-NMR (400 MHz, CDCl3): 7.39-6.86 (m, 7H), 5.39-4.98 (m, 1H), 3.24-2.77 (m, 1H), 2.35 (m, 3H), 2.32-2.09 (m, 1H) ppm.

Workup

concentrationThe reaction mixture was concentrated
customthe residue purified by chromatography on silica gel (eluent: ethyl acetate/heptane)

Sources & evidence

ORD record: ord-c7df234e1e804faa9f78ee30270514f8
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216973B2

Reaction notes

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