Sulfuryl chloride → HCID 19101393, compound

HRID 1975260Notes

Reaction equation

HRID 1975260 reaction equation
S(Cl)(Cl)(=O)=O.[Br:6][C:7]1[CH:8]=[C:9]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:10]=[C:11]([Br:14])[C:12]=1[SH:13].S(Cl)Cl.[CH:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][CH3:33])([CH3:25])[CH3:24].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl.CO>[Br:6][C:7]1[CH:8]=[C:9]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:10]=[C:11]([Br:14])[C:12]=1[S:13][C:30]1[CH:29]=[CH:28][C:27]([O:32][CH3:33])=[C:26]([CH:23]([CH3:25])[CH3:24])[CH:31]=1

Participants

8

Reactant 5

HCID 24648Sulfuryl chlorideHCID 25353Sulfur dichlorideHCID 2706232-IsopropylanisoleHCID 6451240Aluminum(III) ChlorideHCID 19101399Methyl 3,5-dibromo-4-mercaptophenylacetate

Product 1

HCID 19101393HCID 19101393, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Sulfuryl chloride (0.9 mL, 0.011 mol) in 5 mL of dichloromethane was added dropwise to a solution of methyl 3,5-dibromo-4-mercaptophenylacetate (3.4 g, 0.11 mol), from Preparation E, in 50 mL dichloromethane. The pale yellow solution was allowed to stand for 1 hour and transferred to an addition funnel. The resulting sulfenyl chloride was then added dropwise to an ice-cooled suspension of 2-isopropylanisole (1.8 g, 0.022 mol) and aluminum chloride (2.8 g, 0.02 mol) in methanol. The reaction mixture was allowed to warm to room temperature and stirred for an additional 15 min. The reaction mixture was then poured on to ice water and extracted twice with dichloromethane. The combined extract was washed with water and brine, dried (Na2SO4), and evaporated on a rotary evaporator. The residue was purified by flash chromatography (silica gel, 5:1 acetone:hexane) to obtain methyl 3,5-dibromo-4-(3-isopropyl-4-methoxyphenylthio)-phenylacetate (3.5 g, 0.007 mol, 70% yield), MP: 73°-76° C.

Workup

  1. customtransferred to an addition funnel
  2. temperaturecooled
  3. extractionextracted twice with dichloromethane
  4. extractionThe combined extract
  5. washwas washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated on a rotary evaporator
  8. customThe residue was purified by flash chromatography (silica gel, 5:1 acetone:hexane)

Sources & evidence

ORD record
ord-425a00763e3249f08729415c39ea34c6
Source dataset
uspto-grants-1994_02
Patent number
US05284971

Reaction notes

Loading…