Sulfuric Acid → HCID 85957011, compound

HRID 1523759Notes

Reaction equation

HRID 1523759 reaction equation
OS(O)(=O)=O.[CH3:6][C:7](O)([CH3:9])[CH3:8].[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[SH:18].C([O-])(O)=O.[Na+]>CCOCC.O>[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18][C:7]([CH3:9])([CH3:8])[CH3:6]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 805982-BromobenzenethiolHCID 516892Sodium Bicarbonate

Product 1

HCID 85957011HCID 85957011, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

To a 50 mL round-bottomed flask were added a stirbar, water (3.5 mL) and H2SO4 (5.0 mL, 18 M). The flask was then cooled to approximately −10° Celsius and treated with t-BuOH (0.70 mL, 7.5 mmol) followed by 2-bromo-thiophenol (0.60 mL, 5.0 mmol) (drop-wise over three minutes). The resulting mixture was stirred for 24 hours with gradual warming to rt. The reaction mixture was then added to a separatory funnel containing Et2O and sat. NaHCO3. The layers were mixed thoroughly and then separated. The organic layer was washed with 1 N NaOH, dried over MgSO4, filtered and concentrated to dryness. The resulting residue was subjected to FCC gave the title compound (686 mg, 56%). 1H NMR (500 MHz, DMSO-d6) δ 7.75 (dd, J=7.8, 1.4, 1H), 7.68 (dd, J=7.6, 1.6, 1H), 7.43-7.37 (m, 1H), 7.36-7.29 (m, 1H), 1.28 (s, 9H).

Workup

  1. temperaturewith gradual warming to rt
  2. additionThe reaction mixture was then added to a separatory funnel
  3. additionThe layers were mixed thoroughly
  4. customseparated
  5. washThe organic layer was washed with 1 N NaOH
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5172adf5454344919bd9e97c94e8b552
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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