Citric Acid → 2-Bromo-1-[3-tert-butyl-5-(2-methoxyethoxy)phenyl]ethanone

HRID 217715

反応式

HRID 217715 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([C:16](=[O:18])[CH3:17])[CH:8]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br-:19].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(Cl)Cl>CO.C1COCC1>[Br:19][CH2:17][C:16]([C:7]1[CH:8]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)=[O:18]

参加物

6

反応物 4

HCID 311Citric AcidHCID 6344DichloromethaneHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 581368081-[3-Tert-butyl-5-(2-methoxyethoxy)phenyl]ethanone

生成物 1

HCID 581367822-Bromo-1-[3-tert-butyl-5-(2-methoxyethoxy)phenyl]ethanone収率 292.5%

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

1-[3-tert-Butyl-5-(2-methoxyethoxy)phenyl]ethanone (O2.043; 1 g) was dissolved in methanol/THF (25 ml/25 ml), admixed with phenyltrimethylammonium tribromide (882 mg) while stirring and stirred at RT overnight. Then 50 ml of 20% citric acid solution were added and the mixture was stirred for 1 h. Subsequently, DCM (200 ml) was added and the mixture was extracted three times with DCM. Then the combined DCM phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified using silica gel (40 g cartridge, n-heptane/EA gradient of 0-30% in 30 min). 1.31 g of the title compound were obtained.

後処理

  1. stirringstirred at RT overnight
  2. stirringthe mixture was stirred for 1 h
  3. extractionthe mixture was extracted three times with DCM
  4. dry with materialThen the combined DCM phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified
  8. customsilica gel (40 g cartridge, n-heptane/EA gradient of 0-30% in 30 min)

出典と根拠

ORDレコード
ord-a25aebc613cf4db3876963c6003ed612
出典データセット
uspto-grants-2012_06
特許番号
US08198272B2

関連ノート

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