Hydrochloric Acid → 2,6-Dichloro-4-hydroxybenzaldehyde

HRID 1043489

반응식

HRID 1043489 반응식
C([Li])CCC.[Cl:6][C:7]1[CH:8]=[C:9]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[O:10][Si](C(C)C)(C(C)C)C(C)C.CN([CH:28]=[O:29])C.Cl>CCCCCC.C1COCC1>[Cl:24][C:22]1[CH:21]=[C:9]([OH:10])[CH:8]=[C:7]([Cl:6])[C:23]=1[CH:28]=[O:29]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 21594466(3,5-Dichlorophenoxy)tris(propan-2-YL)silaneHCID 178418339Butyllithium

생성물 1

HCID 5283822,6-Dichloro-4-hydroxybenzaldehyde

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

A solution of 2.50 M n-butyllithium in hexane (13.3 mL) was added to a stirred solution of (3,5-dichlorophenoxy)(triisopropyl)silane (10.1 g, 31.6 mmol) in THF (40 mL) under an atmosphere of nitrogen at −78° C. After stirring for 45 min at −78° C., DMF (5 mL) was added slowly. The mixture was allowed to warm to −10° C. After hydrolysis with 2 N HCl, the layers were separated and the aqueous layer separated and extracted with ethyl acetate twice. The combined organic solutions were dried over Na2SO4, filtered and concentrated. To the residue was added hexane (30 mL) and the precipitate was filtered and washed with hexane to give the desired product as a white precipitate. (5.50 g, 91%). LCMS for C2H5Cl2O2(M+H)+: m/z=191.

후처리

  1. temperatureto warm to −10° C
  2. customthe layers were separated
  3. customthe aqueous layer separated
  4. extractionextracted with ethyl acetate twice
  5. dry with materialThe combined organic solutions were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. additionTo the residue was added hexane (30 mL)
  9. filtrationthe precipitate was filtered
  10. washwashed with hexane

출처 및 근거

ORD 기록
ord-973115883ab648fbbcaf68c7ca016da9
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563541B2

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