Ethanol → Ethyl 4-bromo-3-chlorobenzoate

HRID 423311Notes

Reaction equation

HRID 423311 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). MS (ES): no mass ion observed.

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-ead7df1f64d0445abd980f9f9964f2cb
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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