2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl → Methyl 4'-{[tert-butyl(dimethyl)silyl]oxy}-6-isopropoxy-2',6'-dimethylbiphenyl-3-carboxylate

HRID 508008ノート

反応式

HRID 508008 の反応式
[Si:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12](B(O)O)=[C:11]([CH3:19])[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][C:30]=1[O:31][CH:32]([CH3:34])[CH3:33])[C:24]([O:26][CH3:27])=[O:25].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1>C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1.[Cl-].[Na+].O.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]>[Si:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:29]2[C:30]([O:31][CH:32]([CH3:34])[CH3:33])=[CH:21][CH:22]=[C:23]([C:24]([O:26][CH3:27])=[O:25])[CH:28]=2)=[C:11]([CH3:19])[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

8

反応物 3

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 21956810Methyl 3-bromo-4-isopropoxybenzoateHCID 598383324-[(Tert-butyldimethylsilyl)oxy]-2,6-dimethylphenylboronic acid

生成物 1

HCID 59838334Methyl 4'-{[tert-butyl(dimethyl)silyl]oxy}-6-isopropoxy-2',6'-dimethylbiphenyl-3-carboxylate収率 82%

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 10340Sodium Carbonate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

(4-{[tert-Butyl(dimethyl)silyl]oxy}-2,6-dimethylphenyl)boronic acid (500 mg, 1.83 mmol) and methyl 3-bromo-4-isopropoxybenzoate (667 mg, 2.38 mmol) were dissolved in a mixture of 2 M aqueous sodium carbonate solution (2.38 mL) and toluene (20 mL), the air was substituted with argon gas, and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (118 mg, 0.29 mmol) and tris(dibenzylideneacetone)dipalladium(0) (67.0 mg, 0.07 mmol) were added. The reaction mixture was heated under reflux under an argon atmosphere for one day. After cooling the reaction mixture, brine was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane-hexane/ethyl acetate=10/1) to give the title compound (642 mg, yield 82%) as a yellow oil.

後処理

  1. additionwere added
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux under an argon atmosphere for one day
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (hexane-hexane/ethyl acetate=10/1)

出典と根拠

ORDレコード
ord-0fc62c22f2b047b183624c9fd6c501af
出典データセット
uspto-grants-2010_08
特許番号
US07786165B2

反応ノート

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