Benzyl Bromide → 2,3-Dichloro-1-methoxy-4-[(phenylmethyl)thio]benzene

HRID 370968Notes

Reaction equation

HRID 370968 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[SH:11].[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[CH2:14]([S:11][C:3]1[CH:4]=[CH:5][C:6]([O:9][CH3:10])=[C:7]([Cl:8])[C:2]=1[Cl:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 159142692,3-Dichloro-4-methoxybenzene-1-thiol

Product 1

HCID 132901932,3-Dichloro-1-methoxy-4-[(phenylmethyl)thio]benzeneYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6.23 g of 2,3-dichloro-4-methoxythiophenol in 60 ml of sieved-dried dimethylformamide is added to 0.75 g of sodium hydride over a period of 2-3 minutes. After stirring at room temperature for 20 minutes, the yellowish solution is treated with 5.10 g of benzyl bromide at a rate so that the temperature does not rise above 40°. Stirring is continued for an additional 30 minutes. The cloudy mixture is poured onto 200 g of crushed ice with caution and the white precipitate is collected on a filter after 1 hour at 10° C. The air-dried product is recrystallized from acetone-hexane to give 7.8 g of 4-benzylthio-2,3-dichloroanisole as white needles, mp 116°-117° C.

Workup

  1. customdoes not rise above 40°
  2. stirringStirring
  3. waitis continued for an additional 30 minutes
  4. customthe white precipitate is collected on
  5. filtrationa filter after 1 hour at 10° C
  6. customThe air-dried product is recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-326f696cbec5444896240d5a8876b6cb
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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