Hydrochloric Acid → HCID 69473456, compound

HRID 1180449Notes

Reaction equation

[H-].[Na+].Br[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:15])[C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1.Br[CH:17]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:18]([O:20][CH3:21])=[O:19].Cl>C1COCC1.C(OCC)C.C(OCC)(=O)C>[CH3:24][CH:23]([CH3:25])[CH2:22][CH:17]([O:15][CH:10]([C:7]1[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=1)[C:11]([F:14])([F:13])[F:12])[C:18]([O:20][CH3:21])=[O:19]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60% W, 2.16 mmol, 87 mg) was suspended in dry THF and cooled to 0° C. A solution of 1-(4-bromophenyl)-2,2,2-trifluoroethanol from example 69 step 2 was added slowly and stirred at 0° C. over 0.75 h. A solution of methyl 2-bromo-4-methylpentanoate from example 69 step 1 was added and the mixture was allowed to warmed to r.t. and stirred overnight. The reaction was treated with 0.1 N aqueous hydrochloric acid, diluted with diethyl ether and ethyl acetate. The phases are separated and the organic layer was washed with 0.1N aqueous hydrochloric acid then brine and dried over magnesium sulfate. The volatiles were removed unde reduced pressure to yield methyl 4-methyl-2-(2,2,2-trifluoro-1-phenylethoxy)pentanoate that was used without further purification.

Workup

temperatureto warmed to r.t.
stirringstirred overnight
customThe phases are separated
washthe organic layer was washed with 0.1N aqueous hydrochloric acid
dry with materialbrine and dried over magnesium sulfate
customThe volatiles were removed unde reduced pressure

Sources & evidence

ORD record: ord-548fa5fbe9f34f8bbc33871dc950d6e2
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279478B2

Reaction notes

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