Methanol → Methyl 4-bromobenzoate

HRID 928909Notes

Reaction equation

HRID 928909 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:16]O>>[CH3:16][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 114644-Bromobenzoic acid

Product 1

HCID 12081Methyl 4-bromobenzoateYield 97%

Procedure

4-bromobenzoic acid (1.10 g, 5.39 mmol) was dissolved in MeOH (30 mL). Concentrated H2SO4 (140 mL) was added and the reaction was allowed to reflux for a total of 29 hr. The reaction was quenched with dilute Na2CO3 (15 mL) and equal volume of EtOAc. The solution was diluted with brine to promote phase separation. The aqueous layer was extracted a second time with EtoAc. The combined organic layers were dried over anhydrous Na2SO4 and evaporated to dryness to afford 4-bromobenzoic acid methyl ester (1.124 g, 5.22 mmol, 97%). 1H-NMR (CD2Cl2, 500 MHz) δ (ppm): 3.89 (s, 3H); 7.56 (d, J=16.8 Hz, 2H); 7.88 (d, J=16.8 Hz, 2H).

Workup

  1. temperatureto reflux for a total of 29 hr
  2. customThe reaction was quenched with dilute Na2CO3 (15 mL) and equal volume of EtOAc
  3. additionThe solution was diluted with brine
  4. customphase separation
  5. extractionThe aqueous layer was extracted a second time with EtoAc
  6. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-a2b12162e83e49e4ab677a1bab031506
Source dataset
uspto-grants-2016_03
Patent number
US09290791B2

Reaction notes

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