1,2-Dichloroethane → (4-Bromo-2-fluorophenyl)(morpholino)methanone

HRID 2354384ノート

反応式

HRID 2354384 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([F:11])[CH:3]=1.C(Cl)CCl.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[O:8])=[C:4]([F:11])[CH:3]=1

参加物

5

反応物 3

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 3026814-Bromo-2-fluorobenzoic acid

生成物 1

HCID 24705647(4-Bromo-2-fluorophenyl)(morpholino)methanone収率 81%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-Bromo-2-fluorobenzoic acid (5.00 g, 22.8 mmol, 1.00 equiv) and EDC (5.23 g, 27.4 mmol, 1.20 equiv) were dissolved in dichloromethane (100 mL). Morpholine (4.77 mL, 54.8 mmol, 2.40 equiv) was added and the solution was maintained at room temperature for 19 h. The reaction mixture was concentrated en vacuo and diluted with EtOAc and 1N HCl. The phases were separated and the organic phase was washed sequentially with water, saturated NaHCO3, and saturated NaCl. The organic phase was subsequently dried over Na2SO4, filtered and concentrated to afford 5.06 g (81%) of a colorless oil which was used without further purification in the next step. MS (ES) m/e 289 [M+H]+.

後処理

  1. concentrationThe reaction mixture was concentrated en vacuo
  2. additiondiluted with EtOAc and 1N HCl
  3. customThe phases were separated
  4. washthe organic phase was washed sequentially with water, saturated NaHCO3, and saturated NaCl
  5. dry with materialThe organic phase was subsequently dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-0a02bf9418df4bdfa647d5ce8a4e4059
出典データセット
uspto-grants-2010_07
特許番号
US07749998B2

反応ノート

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