Hydrochloric Acid → Methyl (4'-hydroxybiphenyl-3-yl)acetate

HRID 2076592노트

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HRID 2076592 반응식
C(=O)([O-])[O-].[K+].[K+].CC1(C)C(C)(C)OB([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)O1.Br[C:24]1[CH:25]=[C:26]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:27]=[CH:28][CH:29]=1.Cl>CN(C)C(=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:21][C:18]1[CH:17]=[CH:16][C:15]([C:28]2[CH:29]=[CH:24][CH:25]=[C:26]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:27]=2)=[CH:20][CH:19]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 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 67%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 21534740N,N-Dimethylacetamide--water (1/1)용매

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온도
110 °C

실험 절차

Tetrakis(triphenylphosphine)palladium (0) (1.00 g, 0.88 mmol) and potassium carbonate (4.80 g, 37.0 mmol) were added to a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (3.84 g, 17.5 mmol) and methyl (3-bromophenyl)acetate (4.00 g, 17.5 mmol) which was synthesized according to the method described in literature (Muller, R. N. et al., Eur. J. Org. Chem., 2002, vol. 23, pp. 3966-3973) in a mixture of N,N-dimethylacetamide-water (10:1, 66 ml), and the mixture was stirred at 110° C. for 6 hours. After the reaction mixture was poured into 0.2N hydrochloric acid and the mixture was extracted with ethyl acetate, the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=2/1) to give methyl (4′-hydroxy-1,1′-biphenyl-3-yl)acetate (2.83 g, yield: 67%).

후처리

  1. customwas synthesized
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was successively washed with water
  4. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  5. customThe residue obtained
  6. customby removing the solvent under reduced pressure
  7. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-1ea0b1dd82e641009b468057c51ae513
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923573B2

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