Potassium Carbonate → Methyl (4'-hydroxybiphenyl-3-yl)acetate

HRID 2247446ノート

反応式

HRID 2247446 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)O1.Br[C:18]1[CH:19]=[C:20]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:21]=[CH:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C(OCC)(=O)C.[Pd].ClC1[C-](P)C(C2C=CC=CC=2)=C(C2C=CC=CC=2)C=1Cl.[CH-]1C=CC=C1.[Fe+2]>[OH:15][C:12]1[CH:11]=[CH:10][C:9]([C:22]2[CH:23]=[CH:18][CH:19]=[C:20]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:21]=2)=[CH:14][CH:13]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 11746402Methyl 2-(3-bromophenyl)acetate

生成物 1

HCID 59219036Methyl (4'-hydroxybiphenyl-3-yl)acetate収率 93.9%

試薬・触媒・溶媒 3

HCID 178527692HCID 178527692、化合物触媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

10 g of 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)phenol and 12.5 g of methyl 3-bromophenylacetate were dissolved in 150 ml of 1,2-dimethoxyethane, then 14 g of potassium carbonate and 920 mg of dichlorodiphenyl phosphinoferrocene palladium were added thereto, and the mixture was stirred overnight at 70° C. in a nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography, to give 10.336 g of the title compound in the 2:1 hexane-ethyl acetate fraction.

後処理

  1. washwashed with 1N hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-78e8d93d603e49c2bc5b378c16cee729
出典データセット
uspto-grants-2010_03
特許番号
US07687664B2

反応ノート

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