Benzyl Alcohol → HCID 21109715, compound

HRID 1766466Notes

Reaction equation

HRID 1766466 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[K+].Cl>CS(C)=O>[CH2:12]([O:19][C:3]1[C:2]([Br:1])=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acid

Product 1

HCID 21109715HCID 21109715, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
140 °C

Procedure

A suspension of 5-bromo-6-chloro-nicotinic acid (CAS [29241-62-1], 1 g), benzylalcohol (0.686 g) and KOH (1.104 g) in DMSO (4 ml) was stirred at 140° C. for 15 min. DMSO (2 ml) was added and the mixture was stirred at 140° C. for 30 min. The mixture was cooled to room temperature. Ice was added and the mixture was acidified using 1 M HCl. The mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried, filtered and concentrated. The product was purified by flash chromatography (SiO2, CH2Cl2=>CH2Cl2/MeOH 4:1) to give 6-benzyloxy-5-bromo-nicotinic acid (0.308 g) as a white solid.

Workup

  1. stirringthe mixture was stirred at 140° C. for 30 min
  2. temperatureThe mixture was cooled to room temperature
  3. additionIce was added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was purified by flash chromatography (SiO2, CH2Cl2=>CH2Cl2/MeOH 4:1)

Sources & evidence

ORD record
ord-0eb31a1a897d4e2fbf8e399e11d5b7c8
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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