Phosphorus tribromide → HCID 71679889, compound

HRID 2274959Notes

Reaction equation

HRID 2274959 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[C:6]2O.P(Br)(Br)[Br:18]>CN(C=O)C>[Br:18][C:6]1[C:7]([N+:13]([O-:15])=[O:14])=[CH:8][N:9]=[C:10]2[C:5]=1[N:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11]2

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 178487957HCID 178487957, compound

Product 1

HCID 71679889HCID 71679889, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

The compound of Example 2 (132.3 g, 1 eq.) was suspended in DMF (1200 mL) at 20° C. and PBr3 (68 mL, 1.2 eq.) was added over a period of 15 min. The mixture was stirred at 65° C. for 60 min, cooled to 20° C., poured on ice (800 g) and filtered. The product was slurried in ethanol (500 mL), filtered and dried on a rotary evaporator at 65° C., affording a yellow solid (155.8 g; 92% yield).

Workup

  1. temperaturecooled to 20° C.
  2. additionpoured on ice (800 g)
  3. filtrationfiltered
  4. filtrationfiltered
  5. customdried on a rotary evaporator at 65° C.
  6. customaffording a yellow solid (155.8 g; 92% yield)

Sources & evidence

ORD record
ord-fa269a6049a0480c87319d07eca5f48b
Source dataset
uspto-grants-2015_09
Patent number
US09127002B2

Reaction notes

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