Hydrogen Bromide → HCID 20137132, compound

HRID 280179Notes

Reaction equation

HRID 280179 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 adjusted 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. extractionextracted with methylene chloride
  2. extractionThe organic extract
  3. washis washed with sat'd NaCl
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue chromatographed (silica gel, hexane/ether)

Sources & evidence

ORD record
ord-f61d9078c62648c2ab6ce9b3e9cde6f9
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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