Sulfuryl chloride → 2-Chloro-4-(2,2,2-trifluoroethoxy)phenol

HRID 51078노트

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HRID 51078 반응식
[F:1][C:2]([F:13])([F:12])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.S(Cl)([Cl:17])(=O)=O>C(NCC(C)C)C(C)C.C1(C)C=CC=CC=1>[Cl:17][C:7]1[CH:6]=[C:5]([O:4][CH2:3][C:2]([F:12])([F:13])[F:1])[CH:10]=[CH:9][C:8]=1[OH:11]

참가 물질

5

반응물 2

HCID 24648Sulfuryl chlorideHCID 130853484-(2,2,2-Trifluoroethoxy)phenol

생성물 1

HCID 227373642-Chloro-4-(2,2,2-trifluoroethoxy)phenol수율 106.1%

시약·촉매·용매 2

HCID 8085Diisobutylamine촉매HCID 1140Toluene용매

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온도
70 °C

실험 절차

To a 30 ml toluene solution of 4-(2,2,2-trifluoroethoxy)phenol (1.02 g, 5.31 mmol) and diisobutylamine (0.074 ml, 0.42 mmol) was added sulfuryl chloride (0.38 ml, 4.7 mmol). This solution was heated to 70° C. for 2 hr. The solvent was removed under reduced pressure. The residue was diluted with AcOEt and sat. bicarb. solution. The organic layer was separated, and the aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel eluting with 10% AcOEt/hexanes to give the title compound as a pale yellow oil 1.13 g (94%).

후처리

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with AcOEt and sat. bicarb
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice with AcOEt
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica gel eluting with 10% AcOEt/hexanes

출처 및 근거

ORD 기록
ord-155ed8dcc6f14da493eeb5ee528efb71
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713508B2

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