Sulfuric Acid → 2-(4-Bromo-2,6-difluorophenyl)acetamide

HRID 1525918노트

반응식

HRID 1525918 반응식
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([CH2:14][C:15]#[N:16])=[C:9]([F:17])[CH:8]=1.[OH-:18].[NH4+]>C(O)(=O)C>[Br:6][C:7]1[CH:8]=[C:9]([F:17])[C:10]([CH2:14][C:15]([NH2:16])=[O:18])=[C:11]([F:13])[CH:12]=1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 27733112-(4-Bromo-2,6-difluorophenyl)acetonitrile

생성물 1

HCID 712707642-(4-Bromo-2,6-difluorophenyl)acetamide수율 78%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
5 °C

실험 절차

To a solution of sulfuric acid (0.96 mL, 18.1 mmol) in acetic acid (20 mL) was slowly added 2-(4-bromo-2,6-difluorophenyl)acetonitrile (0.84 g, 3.6 mmol) portion-wise while stirring, and the reaction mixture was then stirred for 1 h at 100° C. After cooling to 5° C., the mixture was carefully adjusted to pH 9 with 28-30% aq ammonium hydroxide and then was extracted with chloroform (3×40 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification of the residue by flash chromatography (0-100% ethyl acetate/hexanes) provided the title product (0.71 g, 78%). MS(ES+) m/e 250 [M+H]+; 1H NMR (400 MHz, CD2Cl2) δ ppm 3.60 (s, 2 H) 5.54 (br. s., 2 H) 7.10-7.21 (m, 2 H).

후처리

  1. stirringthe reaction mixture was then stirred for 1 h at 100° C
  2. extractionwas extracted with chloroform (3×40 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by flash chromatography (0-100% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-07fb6d66e8674cfdb885605441fa4bb2
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09084794B2

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