Hydrogen Bromide → HCID 66759457, compound

HRID 1402867Notes

Reaction equation

HRID 1402867 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13](=[O:29])[CH2:14][CH:15]([CH:22](C(O)=O)[C:23]([OH:25])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:7]=[CH:6]2.Br>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13](=[O:29])[CH2:14][CH:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:22][C:23]([OH:25])=[O:24])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 66759551HCID 66759551, compound

Product 1

HCID 66759457HCID 66759457, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-(3-(6-methoxynaphthalen-2-yl)-3-oxo-1-phenylpropyl)malonic acid (0.15 g) in acetic acid (5 ml) was treated with 48% aqueous HBr (2 ml) and heated to 150° C. for 2 h. The solvent and acid were removed by distillation and the residue was partitioned between 10% HCl and ethyl acetate. The organic layer was separated, washed with brine, dried over MgSO4, and evaporated to afford a crude, which was purified by flash chromatography on silica gel to give 5-(6-hydroxy-2-naphthalenyl)-5-oxo-3-phenylpentanoic acid (0.1 g) as pale yellow solid.

Workup

  1. customThe solvent and acid were removed by distillation
  2. customthe residue was partitioned between 10% HCl and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customto afford a crude, which
  8. customwas purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-854d392023f24b3bbf7881cb29cdaa6a
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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