Ethanol → Ethyl 2-(5-bromopyridin-3-yl)acetate

HRID 1521584Notes

Reaction equation

HRID 1521584 reaction equation
OS(O)(=O)=O.[Br:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]#N)[CH:10]=[N:11][CH:12]=1.C(=O)(O)[O-:17].[Na+].[CH2:21]([OH:23])[CH3:22]>>[CH2:21]([O:23][C:14](=[O:17])[CH2:13][C:9]1[CH:10]=[N:11][CH:12]=[C:7]([Br:6])[CH:8]=1)[CH3:22]

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 150054172-(5-Bromopyridin-3-yl)acetonitrile

Product 1

HCID 54116619Ethyl 2-(5-bromopyridin-3-yl)acetate

Conditions

Temperature
90 °C

Procedure

To a mixture of ethanol (10 mL) and conc. H2SO4 (4 mL) was added the title compound from Example 53 Step B (0.50 g, 2.5 mmol) in 3 mL of ethanol at room temperature. The mixture was stirred at 90° C. overnight. The reaction was poured into ice and made basic with saturated aqueous sodium bicarbonate solution. It was then extracted with ethyl acetate (2×30 mL), the organic layer was dried, concentrated and purified by flash chromatography on silica gel (petroleum ether:ethyl acetate=10:1) to give the title compound: LCMS m/z 244 [M+H]+; 1H NMR (300 MHz, CDCl3) δ 8.60 (s, 1H), 8.44 (s, 1H), 7.82 (s, 1H), 4.17-4.20 (m, 2H), 3.61 (s, 2H), 1.27-1.30 (m, 3H).

Workup

  1. additionThe reaction was poured into ice
  2. extractionIt was then extracted with ethyl acetate (2×30 mL)
  3. customthe organic layer was dried
  4. concentrationconcentrated
  5. custompurified by flash chromatography on silica gel (petroleum ether:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-f10189a3ea4146298002f645d4567ce9
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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