Benzyl Bromide → 3-Benzyl-5-methylbenzaldehyde

HRID 337656ノート

反応式

HRID 337656 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 866516833-Benzyl-5-methylbenzaldehyde

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-19fedb06d09447cf994a772536abab49
出典データセット
uspto-grants-2014_11
特許番号
US08889714B2

反応ノート

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