Bromochloromethane → 1-((Chloromethyl)sulfonyl)naphthalene

HRID 2240000Notes

Reaction equation

HRID 2240000 reaction equation
[C:1]1([S:11](Cl)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].Br[CH2:27][Cl:28]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:28][CH2:27][S:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)(=[O:13])=[O:12]

Participants

7

Reactant 4

HCID 6333BromochloromethaneHCID 24437Sodium SulfiteHCID 665601-Naphthalenesulfonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 117366081-((Chloromethyl)sulfonyl)naphthaleneYield 88.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-naphthalene sulfonyl chloride (20.2 g, 89.1 mmol), sodium sulfite (22.5 g, 178 mmol) and sodium bicarbonate (15.1 g, 180 mmol) in water (125 mL) was stirred at 100° C. for one hour. After cooling to ambient temperature for 40 minutes, bromochloromethane (90 mL, 1.4 mol) and tetrabutylammonium bromide (2.87 g, 8.91 mmol) were added. The reaction mixture was then stirred at 75° C. for 14.5 hours. After cooling to ambient temperature, the layers of the reaction mixture were separated, and the organic phase was concentrated. The residue was purified by flash chromatography with 100% ethyl acetate. Hexane was added after concentration to help solidify, and the mixture was again concentrated. Drying at 80° C. in vacuo for 20 minutes yielded 1-chloromethanesulfonyl-naphthalene as a pale yellow solid (19.0 g, 88.8%). MP 103-5° C. Mass Spectrum (+EI, M+) m/z 240.

Workup

  1. temperatureAfter cooling to ambient temperature for 40 minutes
  2. stirringThe reaction mixture was then stirred at 75° C. for 14.5 hours
  3. temperatureAfter cooling to ambient temperature
  4. customthe layers of the reaction mixture were separated
  5. concentrationthe organic phase was concentrated
  6. customThe residue was purified by flash chromatography with 100% ethyl acetate
  7. additionHexane was added
  8. concentrationafter concentration
  9. concentrationthe mixture was again concentrated
  10. customDrying at 80° C. in vacuo for 20 minutes

Sources & evidence

ORD record
ord-d6f55b1f3e8646369894c6777907e600
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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