2-Bromoisovaleric acid → 2-[(2,3-Dichloro-4-methoxyphenyl)sulfanyl]-3-methylbutanoic acid

HRID 1903470Notes

Reaction equation

HRID 1903470 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([Cl:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:5]=1[SH:13].Br[CH:15]([CH:19]([CH3:21])[CH3:20])[C:16]([OH:18])=[O:17]>CN(C)C=O.O>[Cl:3][C:4]1[C:9]([Cl:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:5]=1[S:13][CH:15]([CH:19]([CH3:21])[CH3:20])[C:16]([OH:18])=[O:17]

Participants

6

Reactant 3

HCID 112682-Bromoisovaleric acidHCID 24758Sodium hydrideHCID 159142692,3-Dichloro-4-methoxybenzene-1-thiol

Product 1

HCID 159142702-[(2,3-Dichloro-4-methoxyphenyl)sulfanyl]-3-methylbutanoic acidYield 80.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To 3.13 g of 99% sodium hydride under nitrogen at room temperature is added a solution of 12.26 g of 2,3-dichloro-4-methoxythiophenol in 100 ml of sieve-dried dimethylformamide over 2 minutes. The reaction is stirred for 12 minutes. A solution of 9.56 g of α-bromoisovaleric acid in 85 ml of dimethylformamide is added over 4 minutes. The reaction is stirred at room temperature for 3 hours, cooled in ice, diluted with 500 ml of water and filtered. The solution is cooled and acidified with 3 N hydrochloric acid to give the product. The precipitate is filtered, washed with a small amount of water, dried and recrystallized from acetone-pentane to give 13.14 g of α-(2,3-dichloro-4-methoxyphenylthio)isovaleric acid as a white crystalline powder mp 176.5°-178.5°.

Workup

  1. stirringThe reaction is stirred at room temperature for 3 hours
  2. temperaturecooled in ice
  3. filtrationfiltered
  4. temperatureThe solution is cooled
  5. customto give the product
  6. filtrationThe precipitate is filtered
  7. washwashed with a small amount of water
  8. customdried
  9. customrecrystallized from acetone-pentane

Sources & evidence

ORD record
ord-6d83feeed87648da8cc4bc3b1fc68116
Source dataset
uspto-grants-1984_03
Patent number
US04436748

Reaction notes

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