Benzyl Chloride → Benzyl-4-hydroxyphenylmethylsulfonium bis(trifluoromethane sulfonyl)imide

HRID 506423Notes

Reaction equation

C(Cl)C1C=CC=CC=1.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][S:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22](O)=[CH:21][CH:20]=2)=[CH:12][CH:11]=1.[Li+].[N-:27]([S:35]([C:38]([F:41])([F:40])[F:39])(=[O:37])=[O:36])[S:28]([C:31]([F:34])([F:33])[F:32])(=[O:30])=[O:29].C(OCC)(=O)C>O>[N-:27]([S:28]([C:31]([F:34])([F:32])[F:33])(=[O:30])=[O:29])[S:35]([C:38]([F:41])([F:40])[F:39])(=[O:37])=[O:36].[CH2:18]([SH+:17][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([OH:9])=[CH:15][CH:14]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 7.5 °C

Procedure

30 g (0.11 mol) of benzyl-4-hydroxyphenylmethylsulfonium chloride obtained by reacting benzyl chloride with 4-hydroxyphenylmethyl sulfide was dissolved in 500 mL of water, 33.9 g (0.118 mol) of bis(trifluoromethane sulfonyl)imide lithium and 500 mL of ethyl acetate were added thereto, and then stirred at 5 to 10° C. for two hours. The water layer was removed, the organic layer was dried, and then the reaction solution was concentrated under reduced pressure and dried under vacuum. The resulting oily matter was treated with hexane, and then dried under vacuum again. Then, 44.1 g of benzyl-4-hydroxyphenylmethylsulfonium bis(trifluoromethane sulfonyl)imide was obtained in a white crystal (yield: 76.7%). The melting point was 76 to 80° C.

Workup

customThe water layer was removed
customthe organic layer was dried
concentrationthe reaction solution was concentrated under reduced pressure
customdried under vacuum
additionThe resulting oily matter was treated with hexane
customdried under vacuum again

Sources & evidence

ORD record: ord-8b83190ce1be48069b73c1a0da5be981
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07785768B2

Reaction notes

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