Boron tribromide → HCID 86601162, compound

HRID 1173311Notes

Reaction equation

HRID 1173311 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([Cl:17])=[C:14]([Cl:16])[Cl:15])[CH:8]=1>C(Cl)Cl>[Cl:17][C:13]([C:9]1[CH:8]=[C:7]([OH:6])[CH:12]=[CH:11][CH:10]=1)=[C:14]([Cl:15])[Cl:16]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86601161HCID 86601161, compound

Product 1

HCID 86601162HCID 86601162, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.0 g (12.0 mmol) of boron tribromide in 10 mL of CH2Cl2 was magnetically stirred at 0° C. with an external ice-water bath, while a solution of 2.38 g (10.0 mmol) of the product of Step C in 20 mL CH2Cl2 was slowly added over a period of 1 h. At this point the reaction mixture was allowed to slowly warm to room temperature and stirring was continued for an additional 5 h. The reaction was again cooled to 0° C. and quenched by addition of 40 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 to afford the title compound which was used directly in the next step without further purification.

Workup

  1. additionwas slowly added over a period of 1 h
  2. temperatureThe reaction was again cooled to 0° C.
  3. customquenched by addition of 40 mL water
  4. customThe organic layer was separated
  5. washwashed with 2 N NaOH
  6. extractionextracted with ether
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-4d86abb0b3a94426a51ead6d635245b2
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

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