Hydrochloric Acid → HCID 15338398, compound

HRID 1740267Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[Cl:13][CH:14]([Cl:18])[C:15]([OH:17])=[O:16].[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br.Cl>C1COCC1.CCCCCC.O>[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:14]([Cl:18])([Cl:13])[C:15]([OH:17])=[O:16]

Participants

Conditions

Temperature: -40 °C

Procedure

24.3 g (33.6 ml, 0.240 mol) diisopropylamine was dissolved in 100 ml THF while stirring in a nitrogen atmosphere and it was added dropwise at -50° C. to 100 ml (0.240 mol) of a 2.40 M solution of butyllithium in hexane. It was allowed to reach -10° C. for 10 minutes, a solution of 15.5 g (0.120 mol) dichloroacetic acid in 20 ml THF was then added dropwise at -75° C., it was stirred for 25 minutes at -75° C. and subsequently 93.5 g (55.0 ml, 0.41 mol) 1,5-dibromopentane in 50 ml THF was added in such a way that the temperature increased to -40° C. After 2.5 hours at -40° C. it was hydrolyzed with 10 ml 6 N HCl and the precipitate that formed was dissolved with 20 ml water. The organic phase was washed twice with a small amount of water, dried over magnesium sulfate and the solvent was removed in a vacuum. Flash chromatography of the residue on silica gel (mobile solvent: ethyl acetate/heptane 1:10) yielded 19.5 g (59%) 7-bromo-2,2-dichloroheptanoic acid 5 as a colourless oil.

Workup

stirringit was stirred for 25 minutes at -75° C.
customthe precipitate that formed
washThe organic phase was washed twice with a small amount of water
dry with materialdried over magnesium sulfate
customthe solvent was removed in a vacuum

Sources & evidence

ORD record: ord-03c992948c7346da9516c28b784f4762
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05968982

Reaction notes

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