Acetone → HCID 68716253, compound

HRID 1173322Notes

Reaction equation

HRID 1173322 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([O:15]C)[C:6]=1[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)=O.CC(C)=O.B(Br)(Br)Br>C(Cl)Cl>[C:11]([C:9]1[CH:8]=[C:7]([OH:15])[C:6]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1)([CH3:12])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 180AcetoneHCID 280Carbon DioxideHCID 25134Boron tribromideHCID 68718410HCID 68718410, compound

Product 1

HCID 68716253HCID 68716253, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.9 g (14.8 mmol) of the product of Step A in 30 mL of CH2Cl2 was placed in an external cooling bath containing dry ice and acetone and stirred under a nitrogen atmosphere. A 1.0 M solution of boron tribromide (20 mL, 20.0 mmol) in CH2Cl2 was added dropwise. After the addition was complete, the reaction mixture was stirred an additional 5 min then allowed to warn to room temperature. After stirring 1 h the reaction mixture was poured into 500 mL ice water and was stirred for 30 min. The aqueous layer was separated and extracted with 100 mL CH2Cl2. The organic layers were combined, dried Na2SO4), filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 3% EtOAc-hexanes. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred an additional 5 min
  3. customto warn to room temperature
  4. stirringAfter stirring 1 h the reaction mixture
  5. stirringwas stirred for 30 min
  6. customThe aqueous layer was separated
  7. extractionextracted with 100 mL CH2Cl2
  8. filtrationdried Na2SO4), filtered
  9. customevaporated in vacuo
  10. customThe residue was purified on a silica gel flash chromatography column
  11. washeluted with 3% EtOAc-hexanes
  12. customEvaporation of the purified fractions
  13. customdrying in vacuo

Sources & evidence

ORD record
ord-1bd753a48b4e462aab63e5901f805003
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

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