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

HRID 2218665Notes

Reaction equation

HRID 2218665 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:30])([F:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O>>[F:18][C:19]([F:30])([F:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=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 27343872-(Trifluoromethyl)benzeneboronic acidHCID 52579405-bromomethylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 597700785-(2-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 2-(trifluoromethyl)phenyl boronic acid (0.33 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 C23H17F3: Calcd: C, 78.84 H, 4.89; Found: C, 78.65 H, 4.96. HPLC (ISO80-10M)) t=16.67 min (99%).

Workup

  1. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-d1aa0434c3ec407ab655ea8d2b3939c6
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

Loading…