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

HRID 7009

반응식

HRID 7009 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 21584505Methyl 3-bromo-2-fluorobenzoate수율 84%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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) δ 7.90–7.85 (m, 1H), 7.71–7.65 (m, 1H), 7.10 (dt, 1H, J=8.0, 1.0 Hz) and 3.94 (s, 3H): MS (EI) 232 (M+).

후처리

  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

출처 및 근거

ORD 기록
ord-d6c9ebd1225d4262acc61210cf49b56e
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084168B2

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