Boron tribromide → HCID 12159643, compound

HRID 657535Notes

Reaction equation

HRID 657535 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][CH:10]=1)[CH:7]([C:11]#[N:12])[CH2:6]2.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][CH:10]=1)[CH:7]([C:11]#[N:12])[CH2:6]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 27530153-methoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile

Product 1

HCID 12159643HCID 12159643, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

68.7 g (431.6 mmol) of 3-methoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile dissolved in 1500 mL of dichloromethane are brought to 0° C. There are then added, dropwise, over 1 hour 15 minutes, 863 mL of a 1M solution of boron tribromide in dichloromethane (863 mmol/2 eq.). The mixture is then allowed to come back up to ambient temperature overnight. The mixture is brought back to about 0° C. and is poured onto 1 kg of ice. Stirring is carried out for 30 minutes at ambient temperature, the phases are separated and the aqueous phase is extracted again twice with 500 mL of dichloromethane. The combined organic phases are washed with 600 mL of water and then dried over magnesium sulphate. After filtration and concentration, the desired product is obtained.

Workup

  1. customare brought to 0° C
  2. additionThere are then added
  3. customis brought back to about 0° C.
  4. waitis carried out for 30 minutes at ambient temperature
  5. customthe phases are separated
  6. extractionthe aqueous phase is extracted again twice with 500 mL of dichloromethane
  7. washThe combined organic phases are washed with 600 mL of water
  8. dry with materialdried over magnesium sulphate
  9. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-b38ec9691f6649efa229a82daafe56e1
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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