Hydrochloric Acid → 4-Chloro-2-[3-hydroxy-5-(hydroxymethyl)phenoxy]benzonitrile

HRID 1243674노트

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HRID 1243674 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][CH2:8][C:9]1[CH:10]=[C:11]([OH:16])[CH:12]=[C:13]([OH:15])[CH:14]=1.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20](F)[CH:19]=1.Cl>CN(C=O)C.C(OCC)C.O>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([O:15][C:13]2[CH:14]=[C:9]([CH2:8][OH:7])[CH:10]=[C:11]([OH:16])[CH:12]=2)[CH:19]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 346613,5-Dihydroxybenzyl alcoholHCID 936554-Chloro-2-fluorobenzonitrile

생성물 1

HCID 219304194-Chloro-2-[3-hydroxy-5-(hydroxymethyl)phenoxy]benzonitrile수율 9%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

To a stirred solution of cesium carbonate (11.62 g) in dry DMF (70 ml) was added 5-(hydroxymethyl)-1,3-benzenediol (5 g) followed by 4-chloro-2-fluorobenzonitrile (5 g). The mixture was then stirred and heated at 120° C. for 3 h. The cooled mixture was then poured into water (200 ml) and made acidic by the addition of 2M aqueous hydrochloric acid The products were extracted into ethyl acetate (3×150 ml), and the combined extracts were washed with 10% aqueous potassium carbonate solution (100 ml). The organic extract was collected, dried (MgSO4) and concentrated to dryness. Diethyl ether was added to the residue and the mixture filtered. The filtrate was concentrated to dryness and the residue purified by chromatography (silica, 70% diethyl ether/isohexane) to afford, after trituration with diethyl ether, the sub-title compound (800 mg).

후처리

  1. extractionwere extracted into ethyl acetate (3×150 ml)
  2. washthe combined extracts were washed with 10% aqueous potassium carbonate solution (100 ml)
  3. extractionThe organic extract
  4. customwas collected
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to dryness
  7. additionDiethyl ether was added to the residue
  8. filtrationthe mixture filtered
  9. concentrationThe filtrate was concentrated to dryness
  10. customthe residue purified by chromatography (silica, 70% diethyl ether/isohexane)
  11. customto afford

출처 및 근거

ORD 기록
ord-72539a16a7374c18adf0cfd1f63cd558
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119122B2

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