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

HRID 356506Notes

Reaction equation

HRID 356506 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][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[C:26]([CH3:40])=[CH:25][C:24]=1[SH:41])([CH3:22])([CH3:21])[CH3:20]>C(Cl)(Cl)(Cl)Cl>[C:19]([C:23]1[CH:28]=[C:27]([O:29][CH2:30][CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:34])[CH3:35])[C:26]([CH3:40])=[CH:25][C:24]=1[S:41][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

5

Reactant 3

HCID 8471TriethylamineHCID 101308854-Methylbenzene-1-sulfonyl bromide2×HCID 105943112-Tert-butyl-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-benzenethiol

Product 1

HCID 10791774Toluene-4-thiosulfonic acid S-{2-tert-butyl-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-phenyl}ester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a round bottom flask equipped with a magnetic stirrer and an addition funnel were added tosyl bromide (6.07 g, 26.0 mmol), CCl4 (70 mL) and NEt3 (3.59 mL, 26.0 mmol), and this solution was cooled to 0° C. The 2-tert-butyl-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-benzenethiol material prepared in Example OOO (4.6 g, 13.0 mmol) was dissolved in CCl4 (70 mL) and added dropwise to the tosyl bromide solution. The addition was complete in 3.5 hours, at which time the ice bath was removed and the reaction stirred at room temperature overnight. The mixture was diluted with CH2Cl2 and washed with saturated NH4Cl and dried (MgSO4). The solvent was then evaporated and the residue was submitted to flash chromatography (1:1 CH2Cl2 :hexane) to yield the title compound. 1H NMR (CDCl3) δ 0.04 (s, 6 H), 0.85 (s, 9 H), 1.20 (s, 9 H), 2.01 (s, 3 H), 2.37 (s, 3 H), 3.93 (t, 2 H), 3.99 (t, 2 H), 6.82 (s, 1 H), 7.0 (s, 1 H), 7.19 (d, 2 H), 7.44 (d, 2 H).

Workup

  1. customTo a round bottom flask equipped with a magnetic stirrer and an addition funnel
  2. additionThe addition
  3. customthe ice bath was removed
  4. additionThe mixture was diluted with CH2Cl2
  5. washwashed with saturated NH4Cl
  6. dry with materialdried (MgSO4)
  7. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-0b96d6d321cc4ecf9dfdb5bb36a792ab
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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