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

HRID 2272505ノート

反応式

HRID 2272505 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-8c46bbf9b3cd41b8bcb8e09de7e11426
出典データセット
uspto-grants-2015_09
特許番号
US09120777B2

反応ノート

読み込み中…