4-Methoxybenzyl alcohol → 7-Bromo-2,4-bis(4-methoxybenzyloxy)quinazoline

HRID 2274138Notes

Reaction equation

HRID 2274138 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[H-].[Na+].[Br:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18](Cl)=[N:19][C:20](Cl)=[N:21]2)=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[Br:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([O:8][CH2:7][C:6]3[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[N:19][C:20]([O:8][CH2:7][C:6]3[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[N:21]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 341762487-Bromo-2,4-dichloroquinazoline

Product 1

HCID 674015107-Bromo-2,4-bis(4-methoxybenzyloxy)quinazolineYield 83.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

199.0 ml (1.6 mol) of 4-methoxybenzyl alcohol in 0.5 l of toluene were added dropwise to a suspension of 95.8 g (2.4 mol) of sodium hydride [60% in paraffin oil] in 1.5 l of toluene between 15- and 20° C. The mixture was subsequently stirred at room temperature for a further 1 h. 193.6 g (0.67 mol) of 7-bromo-2,4-dichloroquinazoline were then added in portions, and the reaction mixture was stirred for 48 h. Conventional work-up gave 269.0 g of 7-bromo-2,4-bis(4-methoxybenzyloxy)quinazoline as oil [crude product; was reacted further directly].

Workup

  1. stirringthe reaction mixture was stirred for 48 h

Sources & evidence

ORD record
ord-7904ca9311174cf38d0d1d7bf4fa4301
Source dataset
uspto-grants-2015_09
Patent number
US09126952B2

Reaction notes

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