Triethylamine → Toluene 4-thiosulfonic acid S-[2-tert-butyl-4-(2-methoxymethoxy-ethoxy)-5-methyl-phenyl] ester

HRID 1003870Notes

Reaction equation

HRID 1003870 reaction equation
[S:1](Br)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CCN(CC)CC.[C:19]([C:23]1[CH:28]=[C:27]([O:29][CH2:30][CH2:31][O:32][CH2:33][O:34][CH3:35])[C:26]([CH3:36])=[CH:25][C:24]=1[SH:37])([CH3:22])([CH3:21])[CH3:20]>C(Cl)C(Cl)Cl.CCOC(C)=O>[C:19]([C:23]1[CH:28]=[C:27]([O:29][CH2:30][CH2:31][O:32][CH2:33][O:34][CH3:35])[C:26]([CH3:36])=[CH:25][C:24]=1[S:37][S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 101308854-Methylbenzene-1-sulfonyl bromideHCID 187987002-Tert-butyl-4-(2-methoxymethoxy-ethoxy)-5-methyl-benzenethiol

Product 1

HCID 53987067Toluene 4-thiosulfonic acid S-[2-tert-butyl-4-(2-methoxymethoxy-ethoxy)-5-methyl-phenyl] ester

Reagents, catalysts & solvents 2

HCID 65741,1,2-TrichloroethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of tosyl bromide (21.0 g; 89.32 mmol), 50 mL of trichloroethane and 20 mL of NEt3 was cooled to 0° C. To this solution was added slowly a solution of 12.4 mmol of 2-tert-butyl-4-(2-methoxymethoxy-ethoxy)-5-methyl-benzenethiol (prepared in Example AAAA) in 100 mL of trichloroethane. After 13 hours, the reaction mixture was diluted with EtOAc and washed with brine. The product was purified by flash silica gel chromatography, eluting with EtOAc:hexane (5:95, then switching to 3:7).

Workup

  1. washwashed with brine
  2. customThe product was purified by flash silica gel chromatography
  3. washeluting with EtOAc:hexane (5:95

Sources & evidence

ORD record
ord-3a08b547aca54d118ec6372c114765cd
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

Loading…