Sodium hydride → HCID 13290205, compound

HRID 371004Notes

Reaction equation

HRID 371004 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].[F:14][C:15]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:16]=1[CH2:17]Br>CN(C)C=O>[F:14][C:15]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:16]=1[CH2:17][S:13][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[C:9]([Cl:10])[C:4]=1[Cl:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 159142692,3-Dichloro-4-methoxybenzene-1-thiol

Product 1

HCID 13290205HCID 13290205, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a 1.26 g of sodium hydride in 25 ml dimethylformamide (sieve dried) is added dropwise a solution of 10 of 2,3-dichloro-4-methoxythiophenol in 25 ml dimethylformamide. After the addition is complete, the reaction mixture is stirred for 25 mins and a solution of 10 g of 2,4-difluorobenzyl bromide in 25 ml dimethylformamide is added dropwise. After this addition is complete, the mixture is stirred for 20 mins and cautiously poured onto ice-water. The aqueous mixture is extracted with ethyl ether. The ether extracts are washed, dried over anhydrous magnesium sulfate, filtered and the solvent is removed to give an oil which crystallizes with cooling and trituration with hexane. Two recrystallizations with ethyl acetate-hexane give 5.1 g of (2,3-dichloro-4-methoxyphenyl) 2,4-difluorobenzyl sulfide, mp 86°-88°.

Workup

  1. additionAfter the addition
  2. additionAfter this addition
  3. stirringthe mixture is stirred for 20 mins
  4. additioncautiously poured onto ice-water
  5. extractionThe aqueous mixture is extracted with ethyl ether
  6. washThe ether extracts are washed
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent is removed
  10. customto give an oil which
  11. customcrystallizes
  12. temperaturewith cooling
  13. customTwo recrystallizations with ethyl acetate-hexane

Sources & evidence

ORD record
ord-cc37eb1c64a04869bef9ca725ddc25c4
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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