Ethanol → Ethyl 4-bromo-3-chlorobenzoate

HRID 2189746Notes

Reaction equation

HRID 2189746 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[Cl:11].S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:17][CH3:18])=[O:7])=[CH:4][C:3]=1[Cl:11]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 125943024-Bromo-3-chlorobenzoic acid

Product 1

HCID 12594301Ethyl 4-bromo-3-chlorobenzoate

Procedure

To a suspension of 4-bromo-3-chlorobenzoic acid (5.00 g, 21.2 mmol) in ethanol (50 mL) was added sulphuric acid (5 mL) and the resultant mixture heated to reflux for 60 h. The reaction was partitioned between ethyl acetate (50 mL) and water (50 mL). The aqueous layer was extracted with further ethyl acetate and the combined organic fractions dried (phase separator) and concentrated in vacuo to give the title compound as a brown oil/solid (5.09 g, 19.3 mmol). δH (d6-DMSO, 400 MHz): 8.06 (1H, d), 7.96 (1H, d), 7.80 (1H, dd), 4.33 (2H, q), 1.33 (3H, t).

Workup

  1. temperatureto reflux for 60 h
  2. customThe reaction was partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. extractionThe aqueous layer was extracted with further ethyl acetate
  4. customthe combined organic fractions dried (phase separator)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-070f847254134e65a90b6723cbaf8c2a
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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