2-(Trifluoromethyl)benzeneboronic acid → 2-Chloro-5-(2-trifluoromethyl-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

HRID 2218687Notes

Reaction equation

HRID 2218687 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.Br[CH:15]=[C:16]1[C:22]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=2[CH2:20][CH2:19][C:18]2[CH:28]=[CH:29][CH:30]=[CH:31][C:17]1=2>>[Cl:27][C:25]1[CH:24]=[CH:23][C:22]2[C:16](=[CH:15][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:2]([F:13])([F:12])[F:1])[C:17]3[CH:31]=[CH:30][CH:29]=[CH:28][C:18]=3[CH2:19][CH2:20][C:21]=2[CH:26]=1

Participants

3

Reactant 2

HCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 688868195-bromomethylene-2-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 689407572-Chloro-5-(2-trifluoromethyl-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cyclohepteneYield 90%

Procedure

Following procedures essentially as described in Example 219, below, and using 2-(trifluoromethyl)phenylboronic acid (59 mg, 0.31 mmol) and 5-bromomethylene-2-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (91 mg, 0.28 mmol) provides 97 mg (90%) title compound. GC/MS data: retention times in minutes (MS data for M+.ion): 18.19 (384), 18.38(384)Mass Spec (EI+) 384

Sources & evidence

ORD record
ord-76f4a18afea24a5eae56cf2636d86c11
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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