Water → HCID 57772620, compound

HRID 1522722Notes

Reaction equation

[OH-].[K+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)=[O:12])=[CH:6][CH:5]=1.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([C:30]([C:32]2[CH:37]=[CH:36][C:35]([Br:38])=[CH:34][CH:33]=2)=O)=O)=[CH:24][CH:23]=1.O>C(O)C.ClCCl>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11](=[O:12])[C:13]([C:14]3[CH:15]=[CH:16][C:17]([Br:20])=[CH:18][CH:19]=3)=[C:28]([C:25]3[CH:26]=[CH:27][C:22]([Br:21])=[CH:23][CH:24]=3)[C:30]=2[C:32]2[CH:33]=[CH:34][C:35]([Br:38])=[CH:36][CH:37]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of potassium hydroxide (230 mg, 4.1 mmol) in ethanol (5 cm3) was added to a solution of (13) (3.01 g, 8.2 mmol) and 4,4′-dibromobenzil (3.01 g, 8.2 mmol) in ethanol (45 cm3) at 70° C., and the reaction was stirred at 70° C. for 4 hours. Water (200 cm3) and dichloromethane (200 cm3) were added, and the layers were separated. The organic layer was washed with brine (200 cm3) and dried over magnesium sulfate. The solvent was removed to leave a dark purple solid. The crude product was passed through a plug of silica, and then recrystallised from a dichloromethane/ethanol mixture to give (14) as a dark purple crystalline solid (3.87 g, 68%).

Workup

customthe layers were separated
washThe organic layer was washed with brine (200 cm3)
dry with materialdried over magnesium sulfate
customThe solvent was removed
customto leave a dark purple solid
customrecrystallised from a dichloromethane/ethanol mixture

Sources & evidence

ORD record: ord-e6bd9eb56a2e41f696ed845ac40c4406
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09078330B2

Reaction notes

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