Potassium Bromide → HCID 87301037, compound

HRID 2410456Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](O)=[O:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[Br-].[K+].Cl[O-].[Na+].C(=O)(O)[O-].[Na+]>ClCCl.CC1(C)N([O])C(C)(C)CCC1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH:17]=[O:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of the compound obtained from step d above (9.0 g) in dichloromethane (90 ml), 2,2,6,6-tetramethylpiperidine N-oxyl (58.77 mg) and potassium bromide (447.57 mg) were added at 0° C. under nitrogen atmosphere. A 4% aqueous sodium hypochlorite (3.497 g) was added at pH 8-9 (maintained by adding saturated aqueous sodium bicarbonate solution). The reaction was stirred for 20 minutes at 0° C. Then, the organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with saturated aqueous sodium bicarbonate solution, water, and brine. Finally, the organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound (8.1 g) which was used as such in the next step.

Workup

customThen, the organic layer was separated
extractionthe aqueous layer was extracted with dichloromethane
washThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution, water, and brine
dry with materialFinally, the organic layers were dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-9d74080d69e04f969555b4ce042018b9
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08816073B2

Reaction notes

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