Ethanol → HCID 15222348, compound

HRID 375117Notes

Reaction equation

HRID 375117 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[O:16])CC(OCC)=O.[Na].[Br:20]N1C(=O)CCC1=O.[OH2:28].[CH2:29](O)[CH3:30]>>[Br:20][CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([F:1])([F:17])[F:18])[C:9]([O:16][CH2:29][CH3:30])=[O:28]

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 67184N-bromobutanimideHCID 5360545SodiumHCID 15222347Ethyl 6,6,6-trifluorohexylacetoacetate

Product 1

HCID 15222348HCID 15222348, compound

Procedure

Ethyl 6,6,6-trifluorohexylacetoacetate was added at -35° C. to a solution of sodium (50 moles, 1.15 g) in 150 ml ethanol and stirred for 15 minutes. N-Bromosuccinimide (50 mmoles, 8.9 g) was added. The solution was allowed to warm to room temperature and stirred for 2.5 hours. The mixture was poured into water. The intermediate was extracted with hexane. The solvent was removed. The oil was chromatographed over silica gel eluted with hexane to yield 13.6 g of ethyl 2-bromo-8,8,8-trifluorooctanoate. (MS).

Workup

  1. stirringstirred for 2.5 hours
  2. extractionThe intermediate was extracted with hexane
  3. customThe solvent was removed
  4. customThe oil was chromatographed over silica gel
  5. washeluted with hexane

Sources & evidence

ORD record
ord-cc44ee9a951d458797f49c5d93755ec6
Source dataset
uspto-grants-1996_01
Patent number
US05484780

Reaction notes

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