Benzyl Bromide → 3-Benzyl-5-methylbenzaldehyde

HRID 337656노트

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HRID 337656 반응식
[CH:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([CH3:9])[CH:8]=1)=[O:2].[F-].[Cs+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>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.COCCOC>[CH2:15]([C:5]1[CH:4]=[C:3]([CH:8]=[C:7]([CH3:9])[CH:6]=1)[CH:1]=[O:2])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 25953Cesium fluorideHCID 16217687(3-Formyl-5-methylphenyl)boronic acid

생성물 1

HCID 866516833-Benzyl-5-methylbenzaldehyde

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a DME solution (0.1 M) of (3-formyl-5-methylphenyl)boronic acid (1 eq.) was added cesium fluoride (3 eq.), tetrakis(triphenylphosphine)palladium (0.1 eq.) and benzyl bromide (1.2 eq.). The mixture was refluxed for 3 h, cooled down to RT and quenched with saturated aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate. The combined organic extracts were then washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (SiO2, Hex→7:3 (v/v) Hex:EtOAc) afforded the title compound.

후처리

  1. temperatureThe mixture was refluxed for 3 h
  2. customquenched with saturated aqueous sodium bicarbonate
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe combined organic extracts were then washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customPurification of the crude product by way of flash chromatography (SiO2, Hex→7:3 (v/v) Hex:EtOAc)

출처 및 근거

ORD 기록
ord-19fedb06d09447cf994a772536abab49
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889714B2

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