Potassium Carbonate → HCID 118021550, compound

HRID 518411Notes

Reaction equation

HRID 518411 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.[C:10]([O:13][CH2:14][CH2:15]Br)(=[O:12])[CH3:11].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:10]([O:13][CH2:14][CH2:15][S:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127654-MethoxybenzenethiolHCID 135641-Acetoxy-2-bromoethane

Product 1

HCID 118021550HCID 118021550, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-methoxybenzene-1-thiol (15.7 g, 0.11 mol), 2-bromoethyl acetate (18.8 g, 0.11 mol), and K2CO3 (46.6 g, 0.34 mol) in acetone (200 mL) were stirred at room temperature for 12 h. Then the mixture was filtered. After CH2Cl2 extractive work up and silica gel chromatography chromatography (PE: EA=1:0-10:1) the title compound (21.1 g, 83.3%) was obtained as a colorless oil. 1H NMR: (CDCl3, 400 MHz) δ 7.40 (dd, J1=6.8 Hz, J2=2.0 Hz, 2H), 6.86 (dd, J1=6.8 Hz, J2=2.0 Hz, 2H), 4.18 (t, J=7.2 Hz, 2H), 3.80 (s, 3H), 3.02 (t, J=7.2 Hz, 2H), 2.03 (s, 3H). LCMS: 139.0 (M−87)+

Workup

  1. filtrationThen the mixture was filtered

Sources & evidence

ORD record
ord-2c354ec2cdde464f8664899481aaaf2f
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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