Sodium Carbonate → 6-Methyl-2-[2-(trifluoromethyl)[1,1'-biphenyl]-4-yl]-1-benzothiophene

HRID 2220268Notes

Reaction equation

HRID 2220268 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8](B(O)O)[S:7][C:6]=2[CH:13]=1.Br[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:17]([C:27]([F:30])([F:29])[F:28])[CH:16]=1.[Al].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[C:17]([C:27]([F:28])([F:30])[F:29])[CH:16]=3)[S:7][C:6]=2[CH:13]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 5359268AluminumHCID 18379633HCID 18379633, compoundHCID 53398048(6-Methyl-1-benzothiophen-2-yl)boronic acid

Product 1

HCID 684539646-Methyl-2-[2-(trifluoromethyl)[1,1'-biphenyl]-4-yl]-1-benzothiopheneYield 54.3%

Reagents, catalysts & solvents 4

HCID 15220664Palladium--triphenylphosphane (1/1)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
85 °C

Procedure

To a slurry of 6-methyl-benzo[b]thiophene-2-boronic acid (0.19 g, 0.001 mol) in 10 mL of benzene is added 4-bromo-2-trifluoromethyl-biphenyl ( 0.3g, 0.001 mol). The reaction flask is then covered with aluminum foil to keep out light. To this is added 58 mg of tetrakis(triphenylphosphine-palladium(0), followed by 1 mL of 2.0N sodium carbonate solution. The biphasic mixture is heated at 85° C. for 3 hours with vigorous stirring. The mixture is cooled to room temperature and 10 mL of brine solution is added. The organic layer is separated, dried and concentrated under vacuo to afford 0.2g of 6-methyl-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. customThe organic layer is separated
  3. customdried
  4. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-a9e94fbd2c8e470eb5eaf7e178d9144e
Source dataset
uspto-grants-2008_08
Patent number
US07417065B2

Reaction notes

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