Methanol → Methyl 3-bromo-5-nitrobenzoate

HRID 852527

反応式

HRID 852527 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].O=S(Cl)Cl.[CH3:18]O>>[CH3:18][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=[C:2]([Br:1])[CH:3]=1

参加物

4

反応物 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2393363-Bromo-5-nitrobenzoic acid

生成物 1

HCID 239341Methyl 3-bromo-5-nitrobenzoate収率 94%

実験手順

To a solution of 3-bromo-5-nitro-benzoic acid (D5) (22.3 g, 90.6 mmol, 1 equiv) in MeOH (300 ml) at 0° C. was added SOCl2 (7.9 ml, 108 mmol, 1.2 equiv) dropwise. The resulting solution was stirred at reflux for 4 hours then cooled to room temperature and concentrated in vacuo. The residue was diluted with AcOEt, washed twice with 2N aqueous NaOH solution and once with brine, dried over MgSO4 and concentrated in vacuo to give 3-bromo-5-nitro-benzoic acid methyl ester (D11) (22.1 g, 94%) as a pale brown solid. RT=3.18 min

後処理

  1. temperatureat reflux for 4 hours
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with AcOEt
  4. washwashed twice with 2N aqueous NaOH solution and once with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-af069a73802042128b68719f111f09ae
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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