Ethyl bromoacetate → 14738-27-3

HRID 1371500Notes

Reaction equation

HRID 1371500 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:11]([O:13][C:14](=[O:17])[CH2:15]Br)[CH3:12]>C1COCC1>[CH2:11]([O:13][C:14](=[O:17])[CH2:15][S:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[CH3:12]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 78114-MethylbenzenethiolHCID 24758Sodium hydride

Product 1

HCID 27149214738-27-3Yield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-methylbenzenethiol (5 g, 40.25) in dry THF was added dropwise to a suspension of NaH (60% in mineral oil, 1.98 g, 48.30) in THF at room temperature and stirred for 30 min. under N2 atmosphere. Ethylbromoacetate (4.9 mL, 44.27) was added slowly to this solution and further stirred at room temperature for 3 h. The solvent was removed under vacuum. The residue was dissolved in dil. HCl and extracted by ethylacetate. The combined organic phase was washed successively with saturated NaHCO3 solution, water and brine then dried over Na2SO4. Evaporation of organic phase yielded 8.46 g (99%) colorless oil. 1H NMR (CDCl3): δ 1.22 (t, J=7.2 Hz, 3H), 2.32 (s, 3H), 3.57 (s, 2H), 4.14 (q, J=7.2 Hz, 2H), 7.11 (d, J=8.0 Hz, 2H), 7.33 (d, J=8.0 Hz, 2H). EIMS m/z 210 (M+1), 233 (M+23).

Workup

  1. stirringfurther stirred at room temperature for 3 h
  2. customThe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in dil. HCl
  4. extractionextracted by ethylacetate
  5. washThe combined organic phase was washed successively with saturated NaHCO3 solution, water and brine
  6. dry with materialthen dried over Na2SO4
  7. customEvaporation of organic phase

Sources & evidence

ORD record
ord-434d185a340342c0a97a8d29db017422
Source dataset
uspto-grants-2007_01
Patent number
US07157469B2

Reaction notes

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