Nitromethane → HCID 67234079、化合物

HRID 216171

反応式

HRID 216171 の反応式
[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:4]=2[O:3]1.[N+:14]([CH3:17])([O-:16])=[O:15].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=[CH:17][N+:14]([O-:16])=[O:15])=[CH:10][C:4]=2[O:3]1

参加物

5

反応物 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 27369732,2-Difluoro-5-formylbenzodioxole2 回

生成物 1

HCID 67234079HCID 67234079、化合物収率 56.8%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of 2,2-difluoro-benzo[1,3]dioxole-5-carbaldehyde [5.48 g, 29.44 mmol, Intermediate (60)] and nitromethane (4.78 mL, 88.32 mmol) in acetic acid (90 mL) is added ammonium acetate (5.67 g, 73.6 mmol). The reaction mixture is heated to reflux for 5.5 hours. Acetic acid is removed in vacuo and the residue is added water (20 mL) and extracted with DCM (3×50 mL), organic layers are combined and washed with 2 N sodium hydroxide, water and brine, dried over sodium sulfate and concentrated. The solid obtained is crystallized in methanol/DCM (1:1) to yield intermediate 2,2-difluoro-5-(2-nitro-vinyl)-benzo[1,3]dioxole [3.83 g, Intermediate (61)] as a solid.

後処理

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 5.5 hours
  3. customAcetic acid is removed in vacuo
  4. additionthe residue is added water (20 mL)
  5. extractionextracted with DCM (3×50 mL), organic layers
  6. washwashed with 2 N sodium hydroxide, water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe solid obtained
  10. customis crystallized in methanol/DCM (1:1)

出典と根拠

ORDレコード
ord-3e293bf7de3541ec910ea814153fe2fc
出典データセット
uspto-grants-2012_06
特許番号
US08193183B2

関連ノート

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