4-Bromobenzaldehyde → 2-(4-Bromo-benzylidene)-6-(2-imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

HRID 368301Notes

Reaction equation

HRID 368301 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[CH2:14][CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1.[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1>[OH-].[K+].C(O)C>[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[C:14]2[CH2:13][CH2:12][C:11]3[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:7][CH2:6][N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)[CH:10]=3)[C:15]2=[O:19])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 707414-BromobenzaldehydeHCID 154869126-(2-Imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 544851762-(4-Bromo-benzylidene)-6-(2-imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-oneYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

According to the method of Example 4, 6-(2-imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (0.40 g, 1.6 mmol) was reacted with 4-bromobenzaldehyde (0.433 g, 2.3 mmol) in 2 mL of 4% KOH in ethanol to afford 0.543 g (81%) of the title compound as a coarse white solid, mp 152-153° C.: CI-MS m/e 423, 425 (M+);

Sources & evidence

ORD record
ord-5dba3188ec974c1eb69c0b68956363b3
Source dataset
uspto-grants-2000_10
Patent number
US06133303

Reaction notes

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