Phosphorus pentabromide → HCID 21569099, compound

HRID 1579834Notes

Reaction equation

HRID 1579834 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13](O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=[CH:6]2.P(Br)(Br)(Br)(Br)[Br:21]>>[Br:21][CH:13]([C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

3

Reactant 2

HCID 62678Phosphorus pentabromideHCID 21569133HCID 21569133, compound

Product 1

HCID 21569099HCID 21569099, compound

Procedure

To 0.0476 moles of ethyl 6-methoxy- 2-naphthylglycolate there is added slowly with stirring at 40°-50°C 23 g. (0.053 moles) of phosphorus pentabromide. The mixture is stirred at room temperature for 16 hours, then diluted with 70 ml. of petroleum ether, and poured into 125 ml. of ice-cold water. The organic phase is separated, washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, filtered and the solvent removed in vacuo to obtain ethyl α-bromo-6-methoxy-2-naphthylacetate.

Workup

  1. stirringThe mixture is stirred at room temperature for 16 hours
  2. additiondiluted with 70 ml
  3. customThe organic phase is separated
  4. washwashed with saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c7d77c245ee44c11b05018c091216e66
Source dataset
uspto-grants-1976_01
Patent number
US03931269

Reaction notes

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