Hydrochloric Acid → 1-Bromo-4-cyano-3-methoxy-5-(4-ethyl-benzyl)-benzene

HRID 1038348노트

반응식

HRID 1038348 반응식
C[C:2]([O-:5])(C)C.[K+].[CH2:7]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](OCC)=O)=[CH:11][CH:10]=1)[CH3:8].[Br:21][C:22]1[CH:27]=C(F)[C:25]([C:29]#[N:30])=[C:24](F)[CH:23]=1.[OH-].[Na+].Cl>CN1C(=O)CCC1.CO>[Br:21][C:22]1[CH:27]=[C:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([CH2:7][CH3:8])=[CH:14][CH:13]=2)[C:25]([C:29]#[N:30])=[C:24]([O:5][CH3:2])[CH:23]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27569164-Bromo-2,6-difluorobenzonitrileHCID 23665647Potassium tert-butoxideHCID 53419404Ethyl 2-(4-ethylphenyl)acetate

생성물 1

HCID 583858181-Bromo-4-cyano-3-methoxy-5-(4-ethyl-benzyl)-benzene

시약·촉매·용매 2

HCID 887Methanol용매HCID 13387N-methyl-2-pyrrolidone용매2회

실험 절차

KOtBu (11.8 g) is added to a flask charged with a stir bar and dry NMP (40 mL) and chilled to −10° C. under argon atmosphere. A solution of ethyl (4-ethyl-phenyl)-acetate (10.1 g) and 1-bromo-4-cyano-3,5-difluoro-benzene (11.5 g) in NMP (40 mL) is added at such a rate that the reaction temperature maintains below 10° C. After stirring for 1 hour at room temperature, methanol (50 mL) and 1 M aqueous sodium hydroxide solution (39 mL) are added and the resulting mixture is stirred overnight at 100° C. Then, 4 M aqueous hydrochloric acid (100 mL) is added and the mixture is stirred for another h at 100° C. The methanol fraction is evaporated, water (200 mL) is added to the residue and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are washed twice with water, twice with brine and dried (MgSO4). The solvent is evaporated and the residue is washed with methanol. The insoluble residue is separated by filtration and dried to give the white product.

후처리

  1. additioncharged with a stir bar
  2. custommaintains below 10° C
  3. stirringthe resulting mixture is stirred overnight at 100° C
  4. stirringthe mixture is stirred for another h at 100° C
  5. customThe methanol fraction is evaporated
  6. additionwater (200 mL) is added to the residue
  7. extractionthe resulting mixture is extracted with ethyl acetate
  8. washThe combined organic extracts are washed twice with water, twice with brine
  9. dry with materialdried (MgSO4)
  10. customThe solvent is evaporated
  11. washthe residue is washed with methanol
  12. customThe insoluble residue is separated by filtration
  13. customdried
  14. customto give the white product

출처 및 근거

ORD 기록
ord-a8f6ea36c3b442f6849ce241222ea0ea
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551957B2

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