Potassium Hydroxide → HCID 50992665, compound

HRID 534708Notes

Reaction equation

HRID 534708 reaction equation
[OH-].[K+].[F:3][C:4]1[CH:5]=[C:6]([CH:12]2[CH:17]([N+:18]([O-:20])=[O:19])[CH2:16][CH:15]=[CH:14][CH2:13]2)[CH:7]=[C:8]([F:11])[C:9]=1[F:10].[Br:21]N1C(=O)CCC1=O>CO.CO.C(OC(=O)C)C>[F:3][C:4]1[CH:5]=[C:6]([CH:12]2[C:17]([Br:21])([N+:18]([O-:20])=[O:19])[CH2:16][CH:15]=[CH:14][CH2:13]2)[CH:7]=[C:8]([F:11])[C:9]=1[F:10]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 67184N-bromobutanimideHCID 67134284HCID 67134284, compound

Product 1

HCID 50992665HCID 50992665, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 56 mg (1 mmol) of KOH in 6 ml of methanol was added dropwise a solution of 257 mg (1 mmol) of 3,4,5-trifluoro-1-(6-nitrocyclohex-3-en-1-yl)-benzene from example 2.3 in 4 ml of methanol/ethylacetate (3:1) and the resulting mixture was stirred for 20 min at room temperature. 178 mg (1 mmol) of NBS (N-bromosuccinimide) were added and the mixture was stirred for another 30 min. The solvents were evaporated in vacuo. Column chromatography (SiO2, cyclohexane/ethylacetate 10:1) yielded 312 mg (0.93 mmol, 93% of theory) of the title compound as yellowish crystals.

Workup

  1. stirringthe mixture was stirred for another 30 min
  2. customThe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-625fcc22f86f4b15a0cd310e11b38fab
Source dataset
uspto-grants-2014_10
Patent number
US08853455B2

Reaction notes

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