Methanol → Methyl 5-bromo-2-methylbenzoate

HRID 403696Notes

Reaction equation

HRID 403696 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.[CH3:16]O>C(OCC)(=O)C>[CH3:16][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[CH3:11]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 3460045-Bromo-2-methylbenzoic acid

Product 1

HCID 316201Methyl 5-bromo-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The compound of example 1 (20.3 g, 0.0944 mol) was dissolved in 150 mL methanol and cooled to 0° C. To this reaction mixture, thionyl chloride (28.07 g, 0.236 mol) was added slowly within 15-20 min. The reaction mixture was stirred at room temperature for 2-3 h. After completion of the reaction, MeOH was removed under vacuum. The oily material obtained was dissolved in ethyl acetate and washed with sodium bicarbonate, water and brine and dried over anhydrous sodium sulfate. The organic layer was concentrated to obtain the title compound.

Workup

  1. customwas removed under vacuum
  2. customThe oily material obtained
  3. washwashed with sodium bicarbonate, water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-8c8c5fffb10c460997d692650c46e66a
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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