3-Bromo-4-methylbenzoic acid → t-butyl 3-bromo-4-methylbenzoate

HRID 2356682Notes

Reaction equation

HRID 2356682 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6]>S(Cl)(Cl)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][C:4]([CH3:8])([CH3:5])[CH3:3])=[O:6]

Participants

3

Reactant 1

HCID 821303-Bromo-4-methylbenzoic acid

Product 1

HCID 12051722t-butyl 3-bromo-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

2 g of 3-bromo-4-methylbenzoic acid were suspended in 9.4 g of thionyl chloride and stirred at 60° C. for 2 h. The cooled reaction mixture was concentrated under reduced pressure, taken up in 20 ml of acetonitrile, admixed with 887 mg of lithium tert-butoxide and stirred at room temperature for 20 h. For workup, the reaction mixture was admixed with ethyl acetate and water. The organic phase was removed, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography (silica gel; n-heptane) and afforded tert-butyl 3-bromo-4-methylbenzoate. 1H NMR: 8.0, s, 1H; 7.8, d, 1H, 7.5, d, 1H, 2.4, s, 3H, 1.55, s, 9H.

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. stirringstirred at room temperature for 20 h
  4. customThe organic phase was removed
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography (silica gel; n-heptane)

Sources & evidence

ORD record
ord-7295ad8b73a744b0b581c468a7feaa58
Source dataset
uspto-grants-2010_07
Patent number
US07759366B2

Reaction notes

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