Bromine → 4-Bromo-2,2-dimethyl-3-oxobutyl trifluoroacetate

HRID 965803Notes

Reaction equation

HRID 965803 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([O:5][CH2:6][C:7]([CH3:12])([CH3:11])[C:8](=[O:10])[CH3:9])=[O:4].[Br:15]Br.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[F:1][C:2]([F:13])([F:14])[C:3]([O:5][CH2:6][C:7]([CH3:11])([CH3:12])[C:8](=[O:10])[CH2:9][Br:15])=[O:4]

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 100360782,2-Dimethyl-3-oxobutyl trifluoroacetate

Product 1

HCID 859569444-Bromo-2,2-dimethyl-3-oxobutyl trifluoroacetateYield 32.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 2,2-dimethyl-3-oxobutyl trifluoroacetate (W. C. Lumma, Jr. and O. H. Ma, J. Org. Chem., 1970, 35, 2391-2393, 8.45 g, 39.8 mmol) in chloroform (26 mL) was added bromine (1.93 mL, 37.8 mmol) in chloroform (14 mL) dropwise at room temperature. The resulting mixture was stirred at room temperature for 1 h. The mixture was poured into crashed ice/water, and aqueous Na2S2O3 (20 mL) and aqueous NaH2PO4 (40 mL) were added. After the mixture was extracted with chloroform (3×30 mL), the extract was dried over magnesium sulfate and concentrated. Distillation of the residue at 99-102° C. under diminished pressure (3.4 mmHg) afforded 3.58 g (30%) of the title compound as colorless oil.

Workup

  1. additionThe mixture was poured
  2. additionwere added
  3. extractionAfter the mixture was extracted with chloroform (3×30 mL)
  4. dry with materialthe extract was dried over magnesium sulfate
  5. concentrationconcentrated
  6. distillationDistillation of the residue at 99-102° C. under diminished pressure (3.4 mmHg)

Sources & evidence

ORD record
ord-5f81e929d7ea47ab98b7ccb0991bd8b8
Source dataset
uspto-grants-2005_10
Patent number
US06951867B2

Reaction notes

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