Bromochloromethane → 1-((Chloromethyl)sulfonyl)naphthalene

HRID 2240046Notes

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.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[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 naphthalene-1-sulfonyl chloride (10.0 g, 44 mmoles), sodium sulfite (11.12 g, 88 mmoles), and sodium bicarbonate (7.4 g, 88 mmoles) in water (50 mL) was heated to 100° C. for one hour. The crude sodium sulfinate solution was allowed to cool for 30 minutes, and then treated with bromochloromethane (43 mL, 661 mmoles) and tetra-N-butylammonium bromide (1.4 g, 4.4 mmoles). The resultant mixture was heated to 75° C. overnight. All solvents were removed under vacuum. Compound was recrystallized from CH2Cl2/hexane to give the title compound as an off white solid (10.62 g, 44 mmoles).

Workup

temperatureto cool for 30 minutes
customAll solvents were removed under vacuum
customCompound was recrystallized from CH2Cl2/hexane

Sources & evidence

ORD record: ord-9fc1c65c6ec84335989a732a4a83ae58
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723329B2

Reaction notes

Loading…