t-Butyl bromide → Tert-butyl 2-(4-fluoroanilino)-4-nitrobenzoate

HRID 2191624노트

반응식

HRID 2191624 반응식
CN(C)C(=O)C.[F:7][C:8]1[CH:26]=[CH:25][C:11]([NH:12][C:13]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:14]=2[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:34]([CH3:37])([CH3:36])[CH3:35]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)(=O)C.O>[F:7][C:8]1[CH:26]=[CH:25][C:11]([NH:12][C:13]2[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:14]=2[C:15]([O:17][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:16])=[CH:10][CH:9]=1

참가 물질

8

반응물 4

HCID 10485t-Butyl bromideHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 576678972-(4-Fluoroanilino)-4-nitrobenzoic acid

생성물 1

HCID 68965268Tert-butyl 2-(4-fluoroanilino)-4-nitrobenzoate

시약·촉매·용매 3

HCID 66133Benzyl triethylammonium chloride촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
55 °C

실험 절차

To N,N-dimethylacetamide 15 mL solution of 2-(4-fluoroanilino)-4-nitrobenzoic acid 1.0 g, were added potassium carbonate 9.9 g, benzyltriethylammonium chloride 0.82 g and 2-bromo-2-methylpropane 21 mL at room temperature, and it was stirred at 55° C. for 4 hours. After the reaction mixture was cooled to room temperature,2-bromo-2-methylpropane 21 mL was added to it, and it was stirred at 55° C. for 12 hours. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with water and 10% citric acid aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate=8:1] to give tert-butyl 2-(4-fluoroanilino)-4-nitrobenzoate 1.1 g of red oil.

후처리

  1. additionwas added to it, and it
  2. stirringwas stirred at 55° C. for 12 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. washafter sequential washing with water and 10% citric acid aqueous solution
  6. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-06b2e4c2d8d74843ace974954c3728ae
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08327467B2

반응 노트

불러오는 중…