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Hydrochloric Acid → Methyl 4-cyano-3-hydroxybenzoate

HRID 379022
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인쇄 미리보기

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HRID 379022 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1I)[C:5]([O:7][CH3:8])=[O:6].Cl.[CH3:14][N:15](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:14]([C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[OH:1])#[N:15]
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 10378812Methyl 3-hydroxy-4-iodobenzoate

생성물 1

HCID 16641129Methyl 4-cyano-3-hydroxybenzoate

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물
촉매

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온도
80 °C

실험 절차

A solution of methyl 3-hydroxy-4-iodobenzoate (2.38 g, 7.0 mmol) (as described in Step B) and Zn(CN)2 (0.575 g, 4.9 mmol) in DMF was degassed with argon for 25 minutes. Pd(Ph3P)4 (0.404 g, 0.35 mmol) was added and the mixture heated to 80° C. for 16 hr. The mixture was poured into 1N HCl and extracted with EtOAc (2×), washed with water then brine, dried (MgSO4) and the solvent removed. Chromatography of the residue (silica gel; hexane:EtOAc 9:1) afforded the title compound as a white solid.

후처리

  1. extractionextracted with EtOAc (2×)
  2. washwashed with water
  3. dry with materialbrine, dried (MgSO4)
  4. customthe solvent removed

출처 및 근거

ORD 기록
ord-91c476a90c244af79776c2ac6b291680
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06297239B1

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