Phenol → HCID 54674386, compound

HRID 869825Notes

Reaction equation

HRID 869825 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:17]=1>CN(C=O)C.O>[O:7]([CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:17]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 127522376-Bromomethyl-nicotinic acid methyl ester

Product 1

HCID 54674386HCID 54674386, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of phenol (489 mg, 5.21 mmol) and K2CO3 (1.44 g, 10.4 mmol) in DMF (15 mL) was added methyl 6-(bromomethyl)nicotinate (1.1a) (1.20 g, 5.21 mmol). The reaction was stirred at room temperature for 30 min and then diluted with water to give 1.2a after isolation by vacuum filtration and further drying in vacuo (810 mg): 1H-NMR (400 MHz, CDCl3) δ 9.21 (d, J=2.0 Hz, 1H), 8.34 (dd, J=8.0, 2.0 Hz, 1H), 7.67 (d, J=8.0 Hz, 1H), 7.37-7.26 (m, 2H), 7.05-6.96 (m, 3H), 5.34 (s, 2H), 3.99 (s, 3H); LC-MS (220 nm) >98%, 244.2 [M+H].

Sources & evidence

ORD record
ord-39f3c7c9b3d943a891a53b7a5678b461
Source dataset
uspto-grants-2015_03
Patent number
US08969389B2

Reaction notes

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