Ethanol → 2,5-Diphenyl-3,4-di(4-bromophenyl)cyclopentadienone

HRID 1522717Notes

Reaction equation

HRID 1522717 reaction equation
[OH-:1].[K+].[C:3]1([CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)C(=O)C)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([C:28]([C:30]2[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][CH:31]=2)=O)=O)=[CH:22][CH:21]=1.CO.[CH2:39](O)[CH3:40]>>[C:13]1([C:9]2[C:3](=[O:1])[C:8]([C:7]3[CH:6]=[CH:5][CH:4]=[CH:40][CH:39]=3)=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][CH:31]=3)[C:26]=2[C:23]2[CH:24]=[CH:25][C:20]([Br:19])=[CH:21][CH:22]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 5

HCID 702Ethanol2×HCID 887MethanolHCID 14797Potassium HydroxideHCID 699071,1-DiphenylacetoneHCID 964304,4'-Dibromobenzil

Product 1

HCID 31068682,5-Diphenyl-3,4-di(4-bromophenyl)cyclopentadienoneYield 84%

Procedure

A solution of potassium hydroxide (1.60 g, 29 mmol) in ethanol (30 mL) was added to a warmed (75° C.) solution of diphenylacetone (12.0 g, 57 mmol) and 4,4′-dibromobenzil (21.0 g, 57 mmol) in ethanol (130 mL). The resulting dark brown solution was poured into methanol, and the dark precipitate filtered to give (9) (26.0 g, 84%).

Workup

  1. filtrationthe dark precipitate filtered

Sources & evidence

ORD record
ord-d0bcc0922a174d629d78fb056b0e4f3c
Source dataset
uspto-grants-2015_07
Patent number
US09078330B2

Reaction notes

Loading…