Oxalyl chloride → 3-(3-Fluoro-4-methoxy-phenysulfanyl)-3-methyl-butyroyl chloride

HRID 619609Notes

Reaction equation

HRID 619609 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:10][C:11]([CH3:17])([CH3:16])[CH2:12][C:13](O)=[O:14])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(Cl)(=O)C([Cl:21])=O>C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([S:10][C:11]([CH3:17])([CH3:16])[CH2:12][C:13]([Cl:21])=[O:14])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 218466493-(3-Fluoro-4-methoxy-phenylsulfanyl)-3-methyl-butyric acid2×

Product 1

HCID 179218173-(3-Fluoro-4-methoxy-phenysulfanyl)-3-methyl-butyroyl chlorideYield 88.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 3-(3-fluoro-4-methoxy-phenylsulfanyl)-3-methyl-butyric acid (Compound 201, 3.00 g, 11.6 mmol) in 40 mL of benzene at room temperature was added a solution of oxalyl chloride (2.21 g, 17.4 mmol) in 5 mL of benzene over 30 minutes. After 3 hours, the solution was washed with ice cold 5% aqueous NaOH (CAUTION: a large volume of gas is released during this procedure), followed by ice cold H2O, and finally saturated aqueous NaCl. The solution was dried (Na2SO4) and concentrated under reduced pressure to give 2.83 g of a clear yellow oil. This material was used without further purification in the next step. 1H NMR (300 MHz, CDCl3)δ: 7.27 (2H, m), 6.96 (1H, t, J=8.4 Hz), 3.93 (3H, s), 3.13 (2H, s), 1.42 (6H, s).

Workup

  1. washthe solution was washed with ice cold 5% aqueous NaOH (CAUTION
  2. dry with materialThe solution was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f044985a401f4b4b9c9c8b2a8f2b5542
Source dataset
uspto-grants-1999_09
Patent number
US05958954

Reaction notes

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