Dichloromethane → HCID 54376030, compound

HRID 1871057Notes

Reaction equation

HRID 1871057 reaction equation
C(Cl)Cl.C[O:5][C:6]1[C:7]([CH3:17])=[C:8]([CH:13]=[CH:14][C:15]=1[CH3:16])[C:9]([O:11][CH3:12])=[S:10].B(Br)(Br)Br>CO>[OH:5][C:6]1[C:7]([CH3:17])=[C:8]([CH:13]=[CH:14][C:15]=1[CH3:16])[C:9]([O:11][CH3:12])=[S:10]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 54217787HCID 54217787, compound

Product 1

HCID 54376030HCID 54376030, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 90 ml methylene chloride, was dissolved methyl 3-methoxy-2-methyl-4-methylthiobenzoate in an amount of 10 g (0.044 mole), and the resulting solution was then fed dropwise into 90 ml methylene chloride solution of boron tribromide in an amount of 8.4 ml (0.088 mole) at a temperature ranging from 5 to 10° C. After stirring the mixture for 4 hours at an ambient temperature, the mixture was further fed dropwise with 50 ml methanol under cooling with ice and washed with water and then with saturated saline solution. After drying the mixture with anhydrous magnesium sulfate, the solvent remained therein was distillated out under reduced pressure to obtain methyl 3-hydroxy-2-methyl-4-methylthiobenzoate in an amount of 9.2 g. The yield was 98%.

Workup

  1. customranging from 5 to 10° C
  2. temperatureunder cooling with ice
  3. washwashed with water
  4. dry with materialAfter drying the mixture with anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-82bb3b75e7b842a0b29f94097e9b28be
Source dataset
uspto-grants-2000_08
Patent number
US06100421

Reaction notes

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