Ethanol → HCID 15222348, compound

HRID 1609763Notes

Reaction equation

HRID 1609763 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 moles, 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-7e690287f1fa4b1fbd130dba3e7beaed
Source dataset
uspto-grants-1995_03
Patent number
US05401851

Reaction notes

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