Stannous Chloride → Methyl 3-amino-5-bromobenzoate

HRID 852529

反応式

HRID 852529 の反応式
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[C:6]([Br:13])[CH:5]=1.Cl[Sn]Cl>CO>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:5]=[C:6]([Br:13])[CH:7]=[C:8]([NH2:10])[CH:9]=1

参加物

4

反応物 2

HCID 24479Stannous ChlorideHCID 239341Methyl 3-bromo-5-nitrobenzoate

生成物 1

HCID 18763420Methyl 3-amino-5-bromobenzoate収率 93%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 3-bromo-5-nitro-benzoic acid methyl ester (D11) (12.1 g, 46.5 mmol, 1 equiv) in MeOH (200 ml) was added SnCl2 (44 g, 233 mmol, 5 equiv). The resulting mixture was stirred at reflux for 4 h, cooled to room temperature and concentrated in vacuo. The residue was partitioned between ice-cold AcOEt and H2O. The aqueous phase was basified with 2N aqueous NaOH solution until a white precipitate appeared, then slowly with 12.5N aqueous NaOH solution until this precipitate disappeared. The temperature was kept below 10° C. during this addition. The two layers were separated and the aqueous phase extracted with AcOEt. The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo to give 3-amino-5-bromo-benzoic acid methyl ester (D12) (9.9 g, 93%) as a brown solid.

後処理

  1. temperatureat reflux for 4 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ice-cold AcOEt and H2O
  4. additionThe temperature was kept below 10° C. during this addition
  5. customThe two layers were separated
  6. extractionthe aqueous phase extracted with AcOEt
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f8c6897872374bf189c3b3722ee2d2c3
出典データセット
uspto-grants-2007_08
特許番号
US07253198B2

関連ノート

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