Morpholine → (4-Bromo-2-fluorophenyl)(morpholino)methanone

HRID 216703ノート

反応式

HRID 216703 の反応式
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[C:10]([F:17])[CH:9]=1.FC1C=C(Br)C=CC=1C(Cl)=O.C(N(C(C)C)CC)(C)C.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>C(Cl)Cl.O>[Br:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)=[O:14])=[C:10]([F:17])[CH:9]=1

参加物

8

反応物 5

HCID 8083MorpholineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 3026814-Bromo-2-fluorobenzoic acidHCID 27340264-Bromo-2-fluorobenzoyl chloride

生成物 1

HCID 24705647(4-Bromo-2-fluorophenyl)(morpholino)methanone

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

A solution of 3.8 ml (44 mmol) oxalyl chloride in 30 ml CH2Cl2 is added dropwise to a iced-cooled solution of 4.88 g (21.9 mmol) 4-bromo-2-fluorobenzoic acid in 180 ml CH2Cl2. After complete addition, the cooling bath is removed and stirring maintained for 15 h at RT. The solvent is evaporated to dryness, the resultant colorless residue is dried under vacuum and then diluted with 80 ml CH2Cl2. This solution of 2-Fluoro-4-bromobenzoyl chloride (CAS 151982-51-3) is then added dropwise to a mixture of 9.55 ml (54.7 mmol) of diisopropylethylamine, 2.01 ml (23 mmol) of morpholine in 100 ml CH2Cl2. After 1 h 30, the reaction mixture is diluted with water and the two phases are separated. The aqueous phase is re-extracted with CH2Cl2 and the combined organic extracts are washed with water, saturated brine, dried over Na2SO4, filtered and the filtrate is concentrated in vacuo to afford, after drying in HV, the title compound which is used in the next step without further purification.

後処理

  1. additionAfter complete addition
  2. customthe cooling bath is removed
  3. customThe solvent is evaporated to dryness
  4. customthe resultant colorless residue is dried under vacuum
  5. additiondiluted with 80 ml CH2Cl2
  6. customthe two phases are separated
  7. extractionThe aqueous phase is re-extracted with CH2Cl2
  8. washthe combined organic extracts are washed with water, saturated brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationthe filtrate is concentrated in vacuo
  12. customto afford
  13. customafter drying in HV
  14. customthe title compound which is used in the next step without further purification

出典と根拠

ORDレコード
ord-44bb9fc3e6a9466caf105c986df9a8e3
出典データセット
uspto-grants-2012_06
特許番号
US08193189B2

反応ノート

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