Cesium carbonate → Methyl 5-hydroxy-4'-methyl-[1,1'-biphenyl]-3-carboxylate

HRID 1845263노트

반응식

HRID 1845263 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6](Br)[CH:5]=1.B(O)(O)[C:14]1[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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>[OH:10][C:8]1[CH:9]=[C:4]([C:3]([O:2][CH3:1])=[O:12])[CH:5]=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:7]=1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 79799Tolylboronic acidHCID 53216607Methyl 3-bromo-5-hydroxybenzoate

생성물 1

HCID 58187967Methyl 5-hydroxy-4'-methyl-[1,1'-biphenyl]-3-carboxylate

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

To a stirred solution of 3-bromo-5-hydroxy-benzoic acid methyl ester (4.09 g, 17.7 mmol) and p-tolylboronic acid (2.86 g, 21 mmol) in toluene (36 mL) was added cesium carbonate (7.14 g, 22 mmol) in water (3.6 mL) at room temperature. The mixture was purged with nitrogen, and tetrakis(triphenylphosphine)palladium(0) (1.05 g, 0.906 mmol) was added. The reaction mixture was subjected to microwave irradiation at 110° C. for 1 hour. After cooling, the mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by flash chromatography to afford the title compound.

후처리

  1. additionwas added
  2. customirradiation at 110° C. for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through Celite
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-28ceccff6b804415acd3a680ee7674ba
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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