Potassium Iodide → HCID 18786120, compound

HRID 1107857Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Br[CH:10]([CH2:16][CH2:17][CH3:18])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH:10]([CH2:16][CH2:17][CH3:18])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

Conditions

Temperature: 45 °C

Procedure

13.8 ml (119.6 mmol) of 2-bromophenol, 25 g (119.6 mmol) of ethyl 2-bromopentanoate, 19.8 g (143.3 mmol) of potassium carbonate, 19.8 g (119.6mmol) of potassium iodide and 210 ml of N,N-dimethylformamide are introduced into a 1 l three-necked flask equipped with a reflux condenser. The mixture is heated at 45° C. for 16 hours. 600 ml of water are added and extraction is carried out with ethyl acetate (3×300 ml). The combined organic phases are washed with 200 ml of a molar sodium hydroxide solution, 2×200 ml of water and 300 ml of brine. They are then dried over sodium sulphate, filtered and concentrated under vacuum and the residue is purified by silica flash chromatography (cyclohexane elution) to give 28.5 g (79%) of ethyl 2-(2-bromophenoxy)pentanoate in the form of an oil.

Workup

customequipped with a reflux condenser
extractionextraction
washThe combined organic phases are washed with 200 ml of a molar sodium hydroxide solution, 2×200 ml of water and 300 ml of brine
dry with materialThey are then dried over sodium sulphate
filtrationfiltered
concentrationconcentrated under vacuum
customthe residue is purified by silica flash chromatography (cyclohexane elution)

Sources & evidence

ORD record: ord-2a5fe6647ab449759f3f589cc804b71b
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06063810

Reaction notes

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