Water → Methyl 2-amino-5-bromo-3-methoxybenzoate

HRID 576327

反応式

HRID 576327 の反応式
[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:14]N1C(=O)CCC1=O.O>CN(C=O)C>[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([Br:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

参加物

5

反応物 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 602320Methyl 2-amino-3-methoxybenzoate

生成物 1

HCID 13894022Methyl 2-amino-5-bromo-3-methoxybenzoate収率 86%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of compound 53 (22.4 g, 123 mmol) in DMF (250 mL) was added N-bromosuccinimide (21.9 g, 123 mmol) portionwise at 0° C. The mixture was stirred at 0° C. for 0.5 h. To the mixture was added water and extracted with EtOAc (500 mL×2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the desired compound 54 (27.5 g, 86%) as a white solid.

後処理

  1. extractionextracted with EtOAc (500 mL×2)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-dd0c574c13a842c8a23be71b3f6275b0
出典データセット
uspto-grants-2015_05
特許番号
US09034921B2

関連ノート

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