Nitromethane → HCID 67234079, 화합물

HRID 216171

반응식

HRID 216171 반응식
[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

참가 물질

5

반응물 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 27369732,2-Difluoro-5-formylbenzodioxole2회

생성물 1

HCID 67234079HCID 67234079, 화합물수율 56.8%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3e293bf7de3541ec910ea814153fe2fc
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193183B2

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