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

HRID 2191624ノート

反応式

HRID 2191624 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 66133Benzyl triethylammonium chloride触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
55 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-06b2e4c2d8d74843ace974954c3728ae
出典データセット
uspto-grants-2012_12
特許番号
US08327467B2

反応ノート

読み込み中…