Ethanol → Ethyl 4-bromo-3,5-dihydroxybenzoate

HRID 531007Notes

Reaction equation

HRID 531007 reaction equation
[Br:1][C:2]1[C:10]([OH:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:12].S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[Br:1][C:2]1[C:10]([OH:11])=[CH:9][C:5]([C:6]([O:8][CH2:18][CH3:19])=[O:7])=[CH:4][C:3]=1[OH:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 860234-Bromo-3,5-dihydroxybenzoic acid

Product 1

HCID 57419684Ethyl 4-bromo-3,5-dihydroxybenzoate

Procedure

A mixture of 4-bromo-3,5-dihydroxybenzoic acid (45.0 g), concentrated sulfuric acid (5 mL), and ethanol (300 mL) was heated to reflux for 24 hours. The solvent was distilled off under reduced pressure. The residue was diluted with ethyl acetate and washed with water, a saturated aqueous solution of sodium bicarbonate, and saturated saline in this order. The obtained organic layer was dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained solid was washed with hexane to obtain the title compound (48.3 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. washThe obtained solid was washed with hexane

Sources & evidence

ORD record
ord-0a1690c4e02b4114bb10bf523f3773d4
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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