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

HRID 2247446노트

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HRID 2247446 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 178527692HCID 178527692, 화합물촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-78e8d93d603e49c2bc5b378c16cee729
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687664B2

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