Triethylamine → 2-(4-Fluoro-3-methyl-phenylsulfanyl)-hexanoic acid methyl ester

HRID 1361050Notes

Reaction equation

HRID 1361050 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH:4](Br)[CH2:5][CH2:6][CH2:7][CH3:8].[F:11][C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][C:13]=1[CH3:19].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3](=[O:10])[CH:4]([S:18][C:15]1[CH:16]=[CH:17][C:12]([F:11])=[C:13]([CH3:19])[CH:14]=1)[CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95578Hexanoic acid, 2-bromo-, methyl esterHCID 27590424-Fluoro-3-methylbenzene-1-thiol

Product 1

HCID 597751732-(4-Fluoro-3-methyl-phenylsulfanyl)-hexanoic acid methyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-bromo-hexanoic acid methyl ester (0.500 g, 2.404 mmol) and 4-fluoro-3-methyl-benzenethiol (0.340 g, 2.404 mmol) in 20 mL of dichloromethane, was added triethylamine (3.3 mL, 12.020 mmol). After stirring at room temperature under N2 for 46 h, the reaction mixture was diluted with dichloromethane and washed with 1N HCl and brine. The organic layer dried over anhydrous Na2SO4. After removing the solvent under reduced pressure, the product was isolated by Flash chromatography (silica gel) eluting with 0-20% ethyl acetate/hexanes to give the title compound as colorless oil (0.596 g, 92% yield). LC-MS: tR=11.2 min; m/z 271 (M+H)+.

Workup

  1. washwashed with 1N HCl and brine
  2. dry with materialThe organic layer dried over anhydrous Na2SO4
  3. customAfter removing the solvent under reduced pressure
  4. customthe product was isolated by Flash chromatography (silica gel)
  5. washeluting with 0-20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-370248bfd41946c3800a5f138ec30ae8
Source dataset
uspto-grants-2011_02
Patent number
US07879911B2

Reaction notes

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