Ethanol → 2-Bromo-3-methyl-3'-(trifluoromethyl)biphenyl

HRID 1028983Notes

Reaction equation

HRID 1028983 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1I.CC1(C)C(C)(C)OB([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].CCO>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27606044,4,5,5-Tetramethyl-2-[3-(trifluoromethyl)phenyl]-1,3,2-dioxaborolaneHCID 509981582-Bromo-1-iodo-3-methylbenzene

Product 1

HCID 673259062-Bromo-3-methyl-3'-(trifluoromethyl)biphenyl

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 2-bromo-1-iodo-3-methylbenzene (200 mg, 0.67 mmol), 4,4,5,5-tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (220 mg, 0.81 mmol), sodium carbonate (214 mg, 2.02 mmol) and tetrakis(triphenylphosphine) palladium (38.9 mg, 0.034 mmol) in toluene (2.0 mL)/EtOH (1.2 mL)/Water (0.2 mL) was heated in an oil bath at 80° C. overnight. The reaction was concentrated and the resultant residue purified by column chromatography (100% Hexanes) to yield 2-bromo-3-methyl-3′-(trifluoromethyl)biphenyl.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe resultant residue purified by column chromatography (100% Hexanes)

Sources & evidence

ORD record
ord-da7f9e17a79f471d83fb78fb9d050da7
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

Loading…