Triethylamine → (4-Fluoro-phenylsulfanyl)-acetic acid methyl ester

HRID 1716317Notes

Reaction equation

HRID 1716317 reaction equation
[CH3:1][O:2][C:3](=[O:6])[CH2:4]Br.C(N(CC)CC)C.[F:14][C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:6])[CH2:4][S:21][C:18]1[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 677894-Fluorothiophenol

Product 1

HCID 20627006(4-Fluoro-phenylsulfanyl)-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of bromo acetic acid methyl ester (1.53 g, 0.95 ml, 10.0 mmol) and triethylamine (3.0 ml) in dry THF (25 mL) was added 4-fluoro-benzenethiol (1.62 g, 12.6 mmol) in one portion at room temperature. The resulting mixture was heated to reflux and stirred until the TLC showed the completion of the reaction. The reaction mixture was diluted with EtOAc and washed sequentially with aqueous HCl, water and saturated NaCl solution. The organic phase was then dried over anhydrous Na2SO4 and concentrated under reduced pressure to gave a crude material, which was then purified by a column chromatography with 0˜5% EtOAc in hexanes. MS: 201.3 (M+H)+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. customthe completion of the reaction
  4. washwashed sequentially with aqueous HCl, water and saturated NaCl solution
  5. dry with materialThe organic phase was then dried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6368f73d05e145a5ba5808c88e9e99ef
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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