Boron tribromide → HCID 58828406, compound

HRID 1983574Notes

Reaction equation

HRID 1983574 reaction equation
C[O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68844355HCID 68844355, compound

Product 1

HCID 58828406HCID 58828406, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step 1 (1.07 g, 4.75 mmol) was taken up in a 1 M methylene chloride solution of boron tribromide (20 mL, 20 mmol). After heating at reflux overnight the reaction was quenched by the dropwise addition of methanol (ca., 5 mL), and briefly refluxed. The mixture was then concentrated and the residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was dried (sodium sulfate) and concentrated to afford crude product as a brown solid. Flash chromatography over silica (hexanes/ethyl acetate) afforded 0.891 g (89%) of product a as a near colorless, crystalline solid: 1H NMR (CDCl3) δ 7.42 (t, J=7.7 Hz, 2H), 7.32 (dd, J=8.3, 1.8 Hz, 1H), 7.23 (t, J=7.4 Hz, 1H), 7.12-7.01 (m, 4H), 6.29 (s, 1H) ppm.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux overnight the reaction
  3. customwas quenched by the dropwise addition of methanol (ca., 5 mL)
  4. temperaturebriefly refluxed
  5. concentrationThe mixture was then concentrated
  6. customthe residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  7. dry with materialThe organic layer was dried (sodium sulfate)
  8. concentrationconcentrated
  9. customto afford crude product as a brown solid

Sources & evidence

ORD record
ord-a0d5b668d5d943df8d87379b70861d0d
Source dataset
uspto-grants-2009_06
Patent number
US07541466B2

Reaction notes

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