Ethanol → Ethyl 4-bromo-2-methylbenzoate

HRID 2060466Notes

Reaction equation

HRID 2060466 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[CH2:22](O)[CH3:23]>>[CH2:22]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[CH3:11])[CH3:23]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 995704-Bromo-2-methylbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 22616358Ethyl 4-bromo-2-methylbenzoate

Procedure

25.3 g of 4-bromo-2-methyl benzoic acid and 5 mL of concentrated sulfuric acid were added to 425 mL of ethanol. The mixture was heated at reflux temperature for 3 days. The solution was cooled to room temperature, adjusted to neutral pH with the addition of sodium bicarbonate, and concentrated to ca. 100 mL volume under reduced pressure. The reduced mixture was partitioned between ethyl acetate and water, and the organic phase was successively washed with saturated bicarbonate and brine solutions. The organic fraction was dried over anhydrous sodium sulfate, and concentrated to 28.2 g of a clear liquid product; 1H NMR (200 MHz, CDCl3) δ 7.78-7.73 (d, J=8.2 Hz, 1H), 7.38-7.32 (m, 2H), 4.40-4.28 (q, J=7 Hz, 2H), 2.57 (s, 3H), 1.42-1.35 (t, J=7 Hz, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 3 days
  3. concentrationconcentrated to ca. 100 mL volume under reduced pressure
  4. customThe reduced mixture was partitioned between ethyl acetate and water
  5. washthe organic phase was successively washed with saturated bicarbonate and brine solutions
  6. dry with materialThe organic fraction was dried over anhydrous sodium sulfate
  7. concentrationconcentrated to 28.2 g of a clear liquid product

Sources & evidence

ORD record
ord-468758dfbb1549f7a073c9d2994c378e
Source dataset
uspto-grants-2012_10
Patent number
US08278325B2

Reaction notes

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