3,5-Bis-trifluoromethylphenylboronic acid → 5-(3,5-Bis-trifluoromethyl-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

HRID 2218671Notes

Reaction equation

HRID 2218671 reaction equation
Br[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2.[F:18][C:19]([F:34])([F:33])[C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1>>[F:18][C:19]([F:33])([F:34])[C:20]1[CH:21]=[C:22]([CH:23]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:25]=1)[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2

Participants

3

Reactant 2

HCID 1562653,5-Bis-trifluoromethylphenylboronic acidHCID 52579405-bromomethylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 866039815-(3,5-Bis-trifluoromethyl-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Procedure

Combine 5-bromomethylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (0.5 g, 1.75 mmol) and 3,5-bis (trifluoromethyl)phenyl boronic acid (0.449 g, 1.75 mmol) using procedures essentially as described in Example 219, below. Pass through a plug of silica gel equilibrated with hexanes. Concentrate the filtrate to give the title product. Analysis for C24H16F6: Calcd: C, 68.90 H, 3.85. Found: C, 68.64 H, 3.80. HPLC (ISO80-10M)) t=5.64 min (98%).

Workup

  1. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-7b84394f7c26495db0f0171bfdc96d6a
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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