Hydrogen Bromide → HCID 20137132, compound

HRID 1253155Notes

Reaction equation

HRID 1253155 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:11]C)[CH:3]1[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.Br.O>C(O)(=O)C>[CH3:1][C:2]1([CH3:19])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[OH:11])[CH:3]1[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 20137131HCID 20137131, compound

Product 1

HCID 20137132HCID 20137132, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the 4-methoxy compound from Step 3 above (5 g) and 48% aq. HBr (50 ml) in glacial acetic acid (50 ml) is refluxed for three hours. The mixture is poured into H2O, the pH added to 8-10 and extracted with methylene chloride. The organic extract is washed with sat'd NaCl, dried, filtered, evaporated and the residue chromatographed (silica gel, hexane/ether) affording the desired product as a green solid.

Workup

  1. temperatureis refluxed for three hours
  2. additionthe pH added to 8-10
  3. extractionextracted with methylene chloride
  4. extractionThe organic extract
  5. washis washed with sat'd NaCl
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customthe residue chromatographed (silica gel, hexane/ether)

Sources & evidence

ORD record
ord-de89667b69d2406aa5198693be6d9ff7
Source dataset
uspto-grants-1988_05
Patent number
US04748164

Reaction notes

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