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

HRID 1892595ノート

反応式

HRID 1892595 の反応式
[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]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 76307Phenylglycine nitrile

生成物 1

HCID 450370522-(2-Amino-5-bromophenyl)acetonitrile収率 53.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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 to 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).

後処理

  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)

出典と根拠

ORDレコード
ord-4e756707a08d4897b5b920ce15586339
出典データセット
uspto-grants-2013_08
特許番号
US08507681B2

反応ノート

読み込み中…