Sodium Carbonate → 2,4′-Difluoro-3-(methoxymethoxy)-1,1′-biphenyl

HRID 2272505Notes

Reaction equation

HRID 2272505 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][O:10][CH3:11])[C:3]=1[F:12].[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[F:12][C:3]1[C:4]([O:8][CH2:9][O:10][CH3:11])=[CH:5][CH:6]=[CH:7][C:2]=1[C:17]1[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 90423535HCID 90423535, compound

Product 1

HCID 904236412,4′-Difluoro-3-(methoxymethoxy)-1,1′-biphenylYield 99.7%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1-bromo-2-fluoro-3-(methoxymethoxy)benzene (17.9 g), (4-fluorophenyl)boronic acid (16.0 g), tris(dibenzylideneacetone)dipalladium(0) (3.49 g), a 2 M aqueous sodium carbonate solution (114 mL), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (3.13 g), and toluene (180 mL) was stirred at 100 C for 2 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature and then passed through celite. The organic layer was separated, and the solvent was distilled off under reduced pressure. The obtained residue was passed through a short silica gel (NH) column, and the solvent was distilled off under reduced pressure to obtain the title compound (19.0 g).

Workup

  1. customThe organic layer was separated
  2. distillationthe solvent was distilled off under reduced pressure
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8c46bbf9b3cd41b8bcb8e09de7e11426
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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