Ethanol → Ethyl 6-Bromopicolinate

HRID 1069066Notes

Reaction equation

HRID 1069066 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([OH:15])=[O:14])[N:8]=1.[CH2:16](O)[CH3:17]>C1(C)C=CC=CC=1>[CH2:16]([O:14][C:13]([C:9]1[N:8]=[C:7]([Br:6])[CH:12]=[CH:11][CH:10]=1)=[O:15])[CH3:17]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 5939196-Bromopyridine-2-carboxylic acid

Product 1

HCID 2758810Ethyl 6-Bromopicolinate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sulfuric acid (1.46 mL) was added to a mixture of 2-bromo-6-pyridine-carboxylic acid, ethanol (15 mL) and toluene (30 mL). The reaction heated to reflux for 16 h. The mixture was partitioned between chloroform and a saturated aqueous solution of sodium bicarbonate. The aqueous layer was extracted with chloroform (2 x) and the combined organic layers were dried over sodium sulfate, filtered and concentrated to yield a cloudy orange oil. The oil was purified by silica gel chromatography with 9:1 hexane:ethyl acetate. The title product was obtained as an oily white solid (1.31 g).

Workup

  1. temperatureThe reaction heated
  2. temperatureto reflux for 16 h
  3. customThe mixture was partitioned between chloroform
  4. extractionThe aqueous layer was extracted with chloroform (2 x)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a cloudy orange oil
  9. customThe oil was purified by silica gel chromatography with 9:1 hexane

Sources & evidence

ORD record
ord-384820a3b3a14da094c346cd47d30043
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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