N-bromobutanimide → 2-(2-Amino-5-bromophenyl)acetonitrile

HRID 2281895노트

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HRID 2281895 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].[Br:11]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:11])=[CH:4][C:3]=1[CH2:8][C:9]#[N:10]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 76307Phenylglycine nitrile

생성물 1

HCID 450370522-(2-Amino-5-bromophenyl)acetonitrile수율 53.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To a cooled solution of (2-aminophenyl)acetonitrile (13 g, 98 mmol) in dimethylformamide (150 mL) at 0° C., was added N-bromosuccinimide (19.3 g, 108 mmol) in portions for 30 minutes and maintained at 0° C. for 1 hour. The mixture was diluted with ethyl acetate (300 mL) and washed with water (3×100 mL) and saturated sodium chloride (50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The obtained crude product was purified by column chromatography (100-200 mesh silica gel) using 10% ethyl acetate in petroleum ether as eluent to afford (2-amino-5-bromophenyl)acetonitrile (11 g, 53%) as solid. 1HNMR (CDCl3) δ 7.35 (s, 1H), 7.25 (d, 1H), 6.65 (d, 1H), 3.7 (br, 2H), 3.52 (s, 2H).

후처리

  1. washwashed with water (3×100 mL) and saturated sodium chloride (50 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe obtained crude product
  5. customwas purified by column chromatography (100-200 mesh silica gel)

출처 및 근거

ORD 기록
ord-c1010bd658bf43e186f98a69460eb3e3
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139587B2

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