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2-Chlorobenzenesulfonyl chloride → 2-Chlorobenzene-1-sulfonic acid

HRID 1636503
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HRID 1636503 반응식
C([O:8]C1C=C(O)C=CC=1)C1C=CC=CC=1.C(N(C(C)C)CC)(C)C.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32]([OH:34])(=[O:8])=[O:33]
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참가 물질

5

반응물 3

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 138048Benzyl 3-hydroxyphenyl ether

생성물 1

HCID 135314532-Chlorobenzene-1-sulfonic acid수율 185.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

3-Benzyloxyphenol (2.97 g, 15 mmol), as prepared in the preceding step, in methylene chloride (50 mL) was treated with diisopropylethylamine (2 mL) and 2-chlorobenzenesulfonyl chloride (3.27 g, 15.5 mmol) at 0° C. for 2 h and at room temperature for 2 h. The reaction mixture was diluted with 200 mL of methylene chloride, washed sequentially with saturated NaHCO3 (2×50 mL) and brine (2×50 mL), and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash column chromatography (1:1 hexane:methylene chloride) to give the title compound as a colorless liquid (5.35 g, 95%). 1H-NMR (300 MHz, CDCl3) δ 4.97 (s, 2H), 6.71 (dd, 1H, J=1.1, 4.1 Hz), 6.78 (t, 1H, J=2.3 Hz), 6.85 (dd, 1H, J=1.1,4.1 Hz), 7.17 (t, 1H, J=8.3 Hz), 7.37 (m, 5H), 7.58 (m, 2H), and 7.91 (dd, 1H, J=1.1, 4.1 Hz).

후처리

  1. washwashed sequentially with saturated NaHCO3 (2×50 mL) and brine (2×50 mL)
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash column chromatography (1:1 hexane:methylene chloride)

출처 및 근거

ORD 기록
ord-a2212ee094494d2fb333c88221c4844c
출처 데이터셋
uspto-grants-2000_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06034127

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