Boron tribromide → HCID 71626584, compound

HRID 2199485Notes

Reaction equation

HRID 2199485 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9](/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:4]=1[C:5]([O:7][CH3:8])=[O:6].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9](/[CH:15]=[CH:16]/[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 72713558HCID 72713558, compound

Product 1

HCID 71626584HCID 71626584, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve compound 6 (6 g, 0.0201 mol) in 50 ml dichloromethane, add drop wise BBr3 solution in methylene chloride (24 ml, 1M) at 0° C., react at room temperature for 1 h. Wash the reaction solution with water, dry over anhydrous magnesium sulfate. Filter the solution and remove the solvent by rotary evaporation, dissolve the residue with petroleum ether/diethyl ether and feed the solution to a silica gel column, evaporate the solvent in eluent to obtain 5.4 g white solid (95%). 1H-NMR (400M, CDCl3) δ (ppm): 3.79 (s, 3H), 3.82 (s, 3H), 6.40 (d, J=2.4 Hz, 1H), 6.80 (d, J=2.4 Hz, 1H), 7.15 (dd, J=16 Hz, 2H), 7.28 (t, J=7.2 Hz, 1H), 7.38 (t, J=7.2 Hz, 2H), 7.52 (d, J=7.2 Hz, 2H), 10.28 (s, 1H).

Workup

  1. customreact at room temperature for 1 h
  2. washWash the reaction solution with water
  3. dry with materialdry over anhydrous magnesium sulfate
  4. filtrationFilter the solution
  5. customremove the solvent
  6. customby rotary evaporation
  7. dissolutiondissolve the residue with petroleum ether/diethyl ether
  8. customevaporate the solvent in eluent

Sources & evidence

ORD record
ord-639585297f39406484a35abb351ce046
Source dataset
uspto-grants-2016_06
Patent number
US09359298B2

Reaction notes

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