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Triethylamine → Methyl 3-chloro-4-trifluoromethylsulphonyloxy-benzoate

HRID 746768
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HRID 746768 반응식
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[Cl:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=1O)[C:20]([O:22][CH3:23])=[O:21].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl.CCCCCC>[CH3:23][O:22][C:20](=[O:21])[C:19]1[CH:24]=[CH:25][C:26]([O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])=[C:17]([Cl:16])[CH:18]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 77580Methyl 3-chloro-4-hydroxybenzoate

생성물 1

HCID 21841505Methyl 3-chloro-4-trifluoromethylsulphonyloxy-benzoate

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane
용매
HCID 8058Hexane용매

실험 절차

Add dropwise triflic anhydride (6.7 ml, 39.8 mmol) to a solution of methyl 3-chloro-4-hydroxybenzoate (5.42 g, 29.0 mmol), DMAP (490 mg, 4.0 mmol) and triethylamine (5.6 ml, 40.1 mmol) in anhydrous dichloromethane (200 ml). Stir the mixture at room temperature overnight under nitrogen atmosphere. Quench the mixture by addition of a saturated aq. solution of ammonium chloride. Separate the organic layer and extract the aqueous layer with dichloromethane (×3). Wash the combined organic layers with saturated aq. sodium chloride, dry over anhydrous sodium sulfate, filter and concentrate to yield a crude brown oil. Take up this crude oil in hexane and wash the organic layer with water (×3), dry over anhydrous sodium sulfate, filter and concentrate to. yield the title compound.

후처리

  1. customQuench the mixture
  2. additionby addition of a saturated aq. solution of ammonium chloride
  3. customSeparate the organic layer
  4. extractionextract the aqueous layer with dichloromethane (×3)
  5. washWash the combined organic layers with saturated aq. sodium chloride
  6. dry with materialdry over anhydrous sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate
  9. customto yield a crude brown oil
  10. washwash the organic layer with water (×3)
  11. dry with materialdry over anhydrous sodium sulfate
  12. filtrationfilter
  13. concentrationconcentrate to

출처 및 근거

ORD 기록
ord-12cb95a34db04664bd685eaa8712cbce
출처 데이터셋
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07393868B2

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