Toluene → Biphenyl-3-ylacetic acid methyl ester

HRID 459003

반응식

HRID 459003 반응식
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:12]=[C:13]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:14]=[CH:15][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1>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>[CH3:21][O:20][C:18](=[O:19])[CH2:17][C:13]1[CH:12]=[C:11]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:16]=[CH:15][CH:14]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 11746402Methyl 2-(3-bromophenyl)acetate

생성물 1

HCID 10751722Biphenyl-3-ylacetic acid methyl ester수율 78.8%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회

실험 절차

A mixture of phenylboronic acid (1.000 g, 8.20 mmol), methyl 3-bromophenylacetate (1.691 g, 7.38 mmol), Na2CO3 (1.738 g, 16.4 mmol), tetrakis(triphenylphosphine)palladium(0) (0.474 g, 0.41 mmol), toluene (30 mL), and water (5 mL) was heated under reflux for 20 h. The reaction mixture was diluted with water (20 mL) and the volatiles were removed in vacuo. The aqueous solution was washed with EtOAc (4×20 mL). The organic solutions were combined, washed with 1N NaOH (15 mL) followed by water (15 mL). The organic solution was dried (MgSO4), filtered and concentrated in vacuo. Purification by medium pressure chromatography (79:1 hexanes:EtOAc to 39:1 hexanes:EtOAc) provided biphenyl-3-yl-acetic acid methyl ester (1.316 g).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 20 h
  3. customthe volatiles were removed in vacuo
  4. washThe aqueous solution was washed with EtOAc (4×20 mL)
  5. washwashed with 1N NaOH (15 mL)
  6. dry with materialThe organic solution was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by medium pressure chromatography (79:1 hexanes:EtOAc to 39:1 hexanes:EtOAc)

출처 및 근거

ORD 기록
ord-63ddd0a620504476aec901aa149c9f35
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192979B2

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