Potassium Carbonate → 2-Chloro-4-cyano-5-methoxybenzoic acid

HRID 219876

반응식

HRID 219876 반응식
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[C:9](F)=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[C:15]([O-])([O-])=[O:16].[K+].[K+]>CO>[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[C:9]([O:16][CH3:15])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

참가 물질

4

반응물 2

HCID 11430Potassium CarbonateHCID 67528656Methyl 2-chloro-4-cyano-5-fluorobenzoate

생성물 1

HCID 675283752-Chloro-4-cyano-5-methoxybenzoic acid

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of methyl 2-chloro-4-cyano-5-fluorobenzoate (840 mg; 3.93 mmol; 1 eq.) and K2CO3 (2 717.55 mg; 19.66 mmol; 5 eq.) in MeOH (16.80 mL) was stirred at RT for 24 hours. The reaction mixture was concentrated and the residue was taken up in water. The aqueous layer was washed with EtOAc then the aqueous phase was acidified with HCl cc and extracted with EtOAc. The combined organic phases were washed with water, brine, dried over MgSO4 and concentrated affording the title compound as a yellow solid used without further (0.63 g, 75%). 1H NMR (DMSO-d6, 300 MHz) δ 14.05 (br s, 1H), 8.04 (s, 1H), 7.51 (s, 1H), 3.96 (s, 3H). HPLC (Method A) Rt 3.11 min (Purity 88.5%).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. washThe aqueous layer was washed with EtOAc
  3. extractionextracted with EtOAc
  4. washThe combined organic phases were washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6278cbf234b14c108b446b54b2a79dc3
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202865B2

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