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

HRID 2272505노트

반응식

HRID 2272505 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-8c46bbf9b3cd41b8bcb8e09de7e11426
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120777B2

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