Boron tribromide → HCID 86601168, compound

HRID 1173317Notes

Reaction equation

HRID 1173317 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[C:11]([C:13]([Cl:17])=[C:14]([Cl:16])[Cl:15])[CH:10]=[C:9]([C:18]([Cl:22])=[C:19]([Cl:21])[Cl:20])[CH:8]=1>C(Cl)Cl>[Cl:17][C:13]([C:11]1[CH:12]=[C:7]([OH:6])[CH:8]=[C:9]([C:18]([Cl:22])=[C:19]([Cl:20])[Cl:21])[CH:10]=1)=[C:14]([Cl:16])[Cl:15]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86601166HCID 86601166, compound

Product 1

HCID 86601168HCID 86601168, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 0.153 g (0.6 mmol) of boron tribromide in 0.5 mL of CH2Cl2 was magnetically stirred at 0° C. with an external ice-water bath, while a solution of 0.093 g (0.25 mmol) of the product of Step C in 0.5 mL CH2Cl2 was added over a period of 5 min. The reaction mixture was stirred an additional 30 min at 0° C. then allowed to warm to room temperature and stirring was continued overnight. The reaction was again cooled to 0° C. and quenched by addition of 1.0 mL water. The organic layer was separated and then washed with 2 N NaOH. The aqueous extracts were acidified with 1 N HCl and extracted with ether. The organic extracts were combined, washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 5% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Workup

  1. additionwas added over a period of 5 min
  2. temperatureto warm to room temperature
  3. stirringstirring
  4. waitwas continued overnight
  5. temperatureThe reaction was again cooled to 0° C.
  6. customquenched by addition of 1.0 mL water
  7. customThe organic layer was separated
  8. washwashed with 2 N NaOH
  9. extractionextracted with ether
  10. washwashed with brine
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. customevaporated in vacuo
  14. customThe residue was purified on a silica gel flash chromatography column
  15. washeluted with 5% EtOAc-hexane
  16. customEvaporation of the purified fractions
  17. customdrying in vacuo

Sources & evidence

ORD record
ord-36aaad67a9ac48e8be7604920297096f
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

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