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

HRID 413175

반응식

HRID 413175 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) 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+).

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-41d7a8e3aab14b49a84d863e7faaf206
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566358B2

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