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

HRID 2273974Notes

Reaction equation

HRID 2273974 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-fa1d53a9ecfb473e9acfafbf8169fc59
Source dataset
uspto-grants-2015_09
Patent number
US09126942B2

Reaction notes

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