Bromochloromethane → 1-((Chloromethyl)sulfonyl)naphthalene

HRID 1711391Notes

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

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 was stirred at 100° C. for one hour, allowed to cool to ambient temperatures for 40 minutes, treated with bromochloromethane (90 mL, 1.4 mol) and tetrabutylammonium bromide (2.87 g, 8.91 mmol), stirred at 75° C. for 14.5 hours and cooled to ambient temperatures. The phases were separated and the organic phase was concentrated in vacuo. The resultant residue was purified by flash chromatography with 100% ethyl acetate to give 1-chloromethanesulfonyl-naphthalene as a pale yellow solid, 19.0 g (88.8% yield), mp 103-5° C., Mass Spectrum (+EI, M+) m/z 240. 1HNMR (500 MHz, DMSO-d6): δ8.64-5 (m, 1H), 8.41 (d, 1H, J=8.23 Hz), 8.27 (dd, 1H, J=7.33 Hz and 1.22 Hz), 8.16-8.18 (m, 1H), 7.71-7.81 (m, 3H), 5.40 ppm, (s, 2H). Elemental Analysis for C11H9ClO2S: Calcd: C, 54.89; H, 3.77; N, 0.00; Found: C, 54.98; H, 3.81; N, 0.00.

Workup

temperatureto cool to ambient temperatures for 40 minutes
stirringstirred at 75° C. for 14.5 hours
temperaturecooled to ambient temperatures
customThe phases were separated
concentrationthe organic phase was concentrated in vacuo
customThe resultant residue was purified by flash chromatography with 100% ethyl acetate

Sources & evidence

ORD record: ord-60a4668324cf4ba1924eb647634e083f
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790751B2

Reaction notes

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