Allyltributylstannane → 3-Allyl-4-methyl-benzoic acid methyl ester

HRID 1991016노트

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HRID 1991016 반응식
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[CH2:13]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[CH2:15].[Cl-].[Li+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][C:11]([CH3:12])=[C:2]([CH2:15][CH:14]=[CH2:13])[CH:3]=1

참가 물질

6

반응물 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 7015747Methyl 3-bromo-4-methylbenzoate

생성물 1

HCID 591286443-Allyl-4-methyl-benzoic acid methyl ester수율 101.8%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
95 °C

실험 절차

Argon was bubbled into a solution of methyl 3-bromo-4-methylbenzoate (11.45 g, 50 mmol), allyltributyl-stannane (16.72 g, 50.5 mmol) and lithium chloride (5.30 g, 125 mmol) in DMF (100 mL) with magnetic stirring for 20 minutes. Dichlorobis(triphenyl-phosphine)palladium (0.81 g, 1.16 mmol) was then added and mixture heated at 95° C. for 1.5 hours. After cooling to room temperature, the mixture was partitioned between ether-hexanes (1:1 V/V) and water. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (Isco RediSep 330 g silica gel, 5% then 35% dichloromethane in hexanes) to give 3-allyl-4-methyl-benzoic acid methyl ester (9.68 g, 100%) as a colorless oil.

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between ether-hexanes (1:1 V/V) and water
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (Isco RediSep 330 g silica gel, 5%

출처 및 근거

ORD 기록
ord-1a01e4bda73d4eecab1e40d3e29a28bc
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645764B2

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