Hydrochloric Acid → HCID 54335313, compound

HRID 581980Notes

Reaction equation

HRID 581980 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:10])[CH:6]=[CH:7][C:8]=1[Br:9].Br[CH2:12][C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:10][CH2:12][C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[CH:7][C:8]=1[Br:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66144Ethyl bromopyruvateHCID 510000874-Bromo-3-methoxybenzene-1-thiol

Product 1

HCID 54335313HCID 54335313, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Methoxy-4-bromobenzenethiol (D2) (9.6 g, 44 mmoles) in pyridine (30 ml) was treated with ethyl bromopyruvate (5.9 ml, 46 mmoles) and stirred at room temperature for 1 hr. Dilute hydrochloric acid (100 ml) was added and the product extracted into diethyl ether. The organics were washed with dilute hydrochloric acid then brine and dried (Na2SO4). Evaporation of the solvent followed by flash chromatography on TLC silica gel eluting with dichloromethane gave the title compound (D3) (3.7 g, 25%).

Workup

  1. extractionthe product extracted into diethyl ether
  2. washThe organics were washed with dilute hydrochloric acid
  3. dry with materialbrine and dried (Na2SO4)
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-419d6fb4c619428fa1d0e3db6fac9401
Source dataset
uspto-grants-1999_07
Patent number
US05922733

Reaction notes

Loading…