Benzyl Bromide → Ethyl 5-(benzyloxy)-6-chloronicotinate

HRID 509404Notes

Reaction equation

HRID 509404 reaction equation
[Cl:1][C:2]1[C:12]([OH:13])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCOC(C)=O>C1(C)C=CC=CC=1.CCCCCC>[CH2:20]([O:13][C:12]1[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([CH:11]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 86687988Ethyl 6-chloro-5-hydroxynicotinate

Product 1

HCID 86687989Ethyl 5-(benzyloxy)-6-chloronicotinate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

To a stirred mixture of ethyl 6-chloro-5-hydroxynicotinate (2 g, 0.01 mol) in Toluene (50.0 mL) were added K2CO3 (2.76 g, 0.02 mol, Rankem, India) and benzyl bromide (2 g, 0.0012 mol). The reaction mixture was stirred for 2 h at room temperature. After completion of the reaction (monitored by TLC, 20% EtOAc in hexane), the reaction mixture was quenched with water (50 mL), extracted with EtOAc (50 mL×3). The combined organic layers were dried over anhydrous sodium sulfate and purified by column chromatography, silica gel (60-120 mesh) using 12-16% EtOAc in petroleum ether as the eluent to give the title compound. MS (ESI, positive ion) m/z: 292.2 (M+H).

Workup

  1. customthe reaction mixture was quenched with water (50 mL)
  2. extractionextracted with EtOAc (50 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. custompurified by column chromatography, silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-2c0e79dc558d4baa956ed3d7833010ed
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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