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

HRID 485879Notes

Reaction equation

HRID 485879 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 3N 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-2eedfcf4d8234db5bee5753d181cd127
Source dataset
uspto-grants-1985_08
Patent number
US04537976

Reaction notes

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