Bromide ion → 1-[3-Tert-butyl-5-(3-hydroxy-2,2-dimethylpropoxy)-4-methoxyphenyl]ethanone

HRID 1524567ノート

反応式

HRID 1524567 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([C:14](=[O:16])[CH3:15])[CH:8]=[C:9]([OH:13])[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].C([O:20][CH2:21][C:22]([CH3:26])([CH3:25])[CH2:23]Br)(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[Br-]>CN(C=O)C>[C:1]([C:5]1[CH:6]=[C:7]([C:14](=[O:16])[CH3:15])[CH:8]=[C:9]([O:13][CH2:23][C:22]([CH3:26])([CH3:25])[CH2:21][OH:20])[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 259Bromide ionHCID 10796Cesium carbonateHCID 133577153-Bromo-2,2-dimethylpropyl acetateHCID 581369461-(3-Tert-butyl-5-hydroxy-4-methoxyphenyl)ethanone

生成物 1

HCID 580458811-[3-Tert-butyl-5-(3-hydroxy-2,2-dimethylpropoxy)-4-methoxyphenyl]ethanone収率 42.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

1-(3-tert-Butyl-5-hydroxy-4-methoxyphenyl)ethanone (O3.070; 2.00 g) and 3-bromo-2,2-dimethylpropyl acetate (2.54 g) were dissolved in DMF (15 ml), and cesium carbonate (3.69 g) was added. After stirring at 150° C. and max. 15 bar in a microwave for 2.5 h, a further 0.5 eq. of the bromide was added and the mixture was placed into the microwave at 150° C. for a further 2 h. Then the mixture was concentrated by rotary evaporation and the residue was partitioned between DCM and water. The DCM phase was removed, dried over magnesium sulfate, filtered and concentrated. The residue was purified using silica gel (120 g cartridge, n-heptane/MtB ether gradient of 0-50% within 60 min). 1.17 g of the title compound were obtained.

後処理

  1. waitthe mixture was placed into the microwave at 150° C. for a further 2 h
  2. concentrationThen the mixture was concentrated by rotary evaporation
  3. customthe residue was partitioned between DCM and water
  4. customThe DCM phase was removed
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified
  9. customsilica gel (120 g cartridge, n-heptane/MtB ether gradient of 0-50% within 60 min)

出典と根拠

ORDレコード
ord-87260c9397574af2be29605d307bea42
出典データセット
uspto-grants-2015_07
特許番号
US09079906B2

反応ノート

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