Sodium Iodide → 2-(5-Chloro-2-nitrophenoxy)-5-methoxybenzoic acid, methyl ester

HRID 364176

반응식

HRID 364176 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[I-].[Na+].Cl[C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27]>CN(C=O)C.[Cu]I.[Cu]>[Cl:25][C:23]1[CH:22]=[CH:21][C:20]([N+:26]([O-:28])=[O:27])=[C:19]([CH:24]=1)[O:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

참가 물질

8

반응물 4

HCID 5238Sodium IodideHCID 118992,4-DichloronitrobenzeneHCID 24758Sodium hydrideHCID 4072341Methyl 2-hydroxy-5-methoxybenzoate

생성물 1

HCID 136890962-(5-Chloro-2-nitrophenoxy)-5-methoxybenzoic acid, methyl ester

시약·촉매·용매 3

HCID 23978Copper촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
85 °C

실험 절차

To a solution of 61.8 g of 2-hydroxy-5-methoxybenzoic acid, methyl ester in 700 ml DMF was added 14.96 g of a 60% suspension of sodium hydride in mineral oil. This was followed by addition of 50.88 g of sodium iodide, 64.64 g of copper(I)iodide, and 2.16 g of finely powdered copper metal. The mixture was heated to 85° C., for 15 minutes, then 71.7 g of 2,4-dichloronitrobenzene was added, and the reaction was stirred at 85° C. for 16 hours. The mixture was filtered, and the filtrate concentrated to an oily residue. Sodium thiosulfate, 400 ml of a 20% solution was added, followed by extraction with ethyl acetate (3×400 ml). The combined ethyl acetate extracts were washed with water (2×325 ml), dried over anhydrous sodium sulfate, then evaporated to afford a pale yellow solid, which was triturated with cyclohexane and filtered giving the title compound, mp 114°-116° C.

후처리

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated to an oily residue
  3. additionSodium thiosulfate, 400 ml of a 20% solution was added
  4. extractionfollowed by extraction with ethyl acetate (3×400 ml)
  5. washThe combined ethyl acetate extracts were washed with water (2×325 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. customto afford a pale yellow solid, which
  9. customwas triturated with cyclohexane
  10. filtrationfiltered

출처 및 근거

ORD 기록
ord-b096b84c5f1f40f39666b10f5de8f91b
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04604390

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