p-Toluenesulfonic acid → Methyl 3-bromo-2-fluorobenzoate

HRID 413175

反応式

HRID 413175 の反応式
[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:12]OC(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:12])=[O:6]

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 27363133-Bromo-2-fluorobenzoic acid

生成物 1

HCID 21584505Methyl 3-bromo-2-fluorobenzoate収率 84%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 3-bromo-2-fluorobenzoic acid (0.219 g, 1 mmol) in dry methanol (5 mL) under nitrogen was treated with trimethylorthoformate (0.22 mL, 2 mmol) and p-toluenesulfonic acid (catalytic amount), and then heated under reflux. After 16 h, the mixture was evaporated and the residue partitioned between water and Et2O. the organic layer was washed with sat. sodium hydrogen carbonate solution, water, brine, dried (MgSO4) and evaporated to give methyl 3-bromo-2-fluorobenzoate (0.195 g, 0.84 mmol, 84%): 1H-NMR (CDCl3) δ7.90-7.85 (m, 1H), 7.71-7.65 (m, 1H), 7.10 (dt, 1H, J=8.0, 1.0 Hz), 3.94 (s, 3H): MS (EI) 232 (M+).

後処理

  1. temperatureheated
  2. temperatureunder reflux
  3. customthe mixture was evaporated
  4. customthe residue partitioned between water and Et2O
  5. washthe organic layer was washed with sat. sodium hydrogen carbonate solution, water, brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

出典と根拠

ORDレコード
ord-41d7a8e3aab14b49a84d863e7faaf206
出典データセット
uspto-grants-2003_05
特許番号
US06566358B2

関連ノート

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