Sulfuryl chloride → 3-Chloro-5-(phenylmethoxy)benzenesulfonyl chloride

HRID 2273974노트

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HRID 2273974 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11](Br)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:17](Cl)([Cl:20])(=[O:19])=[O:18]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:17]([Cl:20])(=[O:19])=[O:18])[CH:12]=[C:13]([Cl:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 24648Sulfuryl chlorideHCID 532170081-(Benzyloxy)-3-bromo-5-chlorobenzene

생성물 1

HCID 581587373-Chloro-5-(phenylmethoxy)benzenesulfonyl chloride수율 62%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Under N2 atmosphere, 2.23 g 1-benzyloxy-3-bromo-5-chloro-benzene was dissolved in 50 mL dry THF, and the mixture was cooled in an ice bath. Dropwise, 14.84 mL of a 1M solution of isopropyl magnesium chloride—lithium chloride complex was added, and the mixture was stirred at room temperature overnight. After cooling to −40° C., 2.41 mL of sulfuryl chloride was added in one portion (T raised to 10° C.), and the mixture was stirred for 15 minutes at room temperature. After cooling with an ice bath, the mixture was quenched with water and acidified with 1M aqueous HCl. The mixture was extracted with MTBE, and the organic phase was dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (PA→PA/Et2O 95:5) to yield 1.53 g (62%) of a colorless oil. 1H NMR (400 MHz, CDCl3) δ 5.14 (s, 2H), 7.30 (t, J=2 Hz, 1H), 7.34-7.47 (m, 5H), 7.50 (t, J=2 Hz, 1H), 7.62 (t, J=1.5 Hz, 1H).

후처리

  1. temperaturethe mixture was cooled in an ice bath
  2. temperatureAfter cooling to −40° C.
  3. stirringthe mixture was stirred for 15 minutes at room temperature
  4. temperatureAfter cooling with an ice bath
  5. customthe mixture was quenched with water
  6. extractionThe mixture was extracted with MTBE
  7. dry with materialthe organic phase was dried over Na2SO4
  8. customevaporated to dryness
  9. customThe residue was purified by flash chromatography (PA→PA/Et2O 95:5)

출처 및 근거

ORD 기록
ord-fa1d53a9ecfb473e9acfafbf8169fc59
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126942B2

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