Hydrochloric Acid → 2-Propoxyethyl 4-Bromobenzenesulfonate

HRID 1058751노트

반응식

HRID 1058751 반응식
[CH2:1]([O:4][CH2:5][CH2:6][OH:7])[CH2:2][CH3:3].C(N(CC)CC)C.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl>ClCCl.O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O:7][CH2:6][CH2:5][O:4][CH2:1][CH2:2][CH3:3])(=[O:24])=[O:23])=[CH:18][CH:17]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 17756Glycol monopropyl ether

생성물 1

HCID 227079362-Propoxyethyl 4-Bromobenzenesulfonate수율 48%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-propoxy-1-ethanol (1.5 g, 14.4 mmol) and triethylamine (2.2 g, 21.6 mmol) in dichloromethane (20 mL) at 0° C. was added 4-bromobenzenesulfonyl chloride (3.86 g, 15.1 mmol) in dichloromethane (10 mL) dropwise over 30 minutes. The reaction was then warmed to room temperature and stirred for 16 hours. The mixture was then poured into water (50 mL) and acidified with 2N aqueous hydrochloric acid (15 mL). The aqueous layer was extracted with dichloromethane and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give a crude residue. This was purified by column chromatography on silica gel (50 g), eluting with hexane:ethyl acetate (9:3), to give the title compound (2.2 g, 48%) as a colourless oil.

후처리

  1. extractionThe aqueous layer was extracted with dichloromethane
  2. dry with materialthe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a crude residue
  6. customThis was purified by column chromatography on silica gel (50 g)
  7. washeluting with hexane:ethyl acetate (9:3)

출처 및 근거

ORD 기록
ord-c89d7cc853f34728b8f8c96a8a5e393d
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06518282B1

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