Benzyl Bromide → HCID 20205048, compound

HRID 978077Notes

Reaction equation

HRID 978077 reaction equation
CN(C)[C:3](=O)[S:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:6]=1[C:13]([O:15][CH3:16])=[O:14].C[O-].[Na+].BrC[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CO>[CH2:3]([S:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:6]=1[C:13]([O:15][CH3:16])=[O:14])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10942334Sodium MethoxideHCID 20205060HCID 20205060, compound

Product 1

HCID 20205048HCID 20205048, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of S-2-carbomethoxy-3-methoxyphenyl dimethylthiocarbamate (1.2 g, 4.5 mmol) and sodium methoxide (0.24 g, 4.5 mmol) in methanol (10 ml) was stirred at reflux temperature under a nitrogen atmosphere for 4 hours. α-Bromotoluene (0.60 ml, 4.9 mmol) was then added, and heating was maintained for an additional hour. The cooled mixture was evaporated, and the residue partitioned between diethyl ether and water. The organic layer was separated and washed with 1% aqueous sodium hydroxide solution, water, saturated aqueous sodium chloride solution, dried (sodium sulfate), and evaporated. The residue was vacuum filtered through a pad of silica gel (Merck No. 7734), eluting successively with 10:1 and 5:1 hexane-ether. Evaporation of the appropriate fractions gave methyl 2-benzylthio-6-methoxybenzoate as a colorless syrup; yield (0.70 g, 54%); NMR (CDCl3, 60 MHz): δ4.06 (s, SCH2Ph) p.p.m.

Workup

  1. temperatureat reflux temperature under a nitrogen atmosphere for 4 hours
  2. temperatureheating
  3. temperaturewas maintained for an additional hour
  4. customThe cooled mixture was evaporated
  5. customthe residue partitioned between diethyl ether and water
  6. customThe organic layer was separated
  7. washwashed with 1% aqueous sodium hydroxide solution, water, saturated aqueous sodium chloride solution
  8. dry with materialdried (sodium sulfate)
  9. customevaporated
  10. filtrationfiltered through a pad of silica gel (Merck No
  11. wash7734), eluting successively with 10:1 and 5:1 hexane-ether
  12. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-607767f004fe4df3a07eb715cb8e788f
Source dataset
uspto-grants-1987_05
Patent number
US04663344

Reaction notes

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