Bromide ion → HCID 18918461, compound

HRID 743820Notes

Reaction equation

HRID 743820 reaction equation
[C:1]([C:4]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:6]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:5]=1)(=[O:3])[CH3:2].[Br-:24]>C(OCC)(=O)C>[Br:24][CH2:2][C:1]([C:4]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:6]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 259Bromide ionHCID 18918270HCID 18918270, compound

Product 1

HCID 18918461HCID 18918461, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product from step (i) above (4.91 g) and cuptic bromide (6.82 g) in ethyl acetate (45 ml) was heated at reflux temperature for 24 hours. On cooling, the mixture was filtered and the liltrate concentrated in vacuo. The residue on purification by flash chromatography on silica, eluting with 5% v/v ethyl acetate/hexane, gave methyl 4-bromoacetyl-2,6-di-tert-butylphenoxyacetate, 4.98 g, as an oil: NMR (d6DMSO) δ7.90 (2H, s), 4.92 (2H, s), 4.40 (2H, s), 3.76 (3H, s), 1.41 (18H, s).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 24 hours
  3. temperatureOn cooling
  4. filtrationthe mixture was filtered
  5. concentrationthe liltrate concentrated in vacuo
  6. customThe residue on purification by flash chromatography on silica
  7. washeluting with 5% v/v ethyl acetate/hexane

Sources & evidence

ORD record
ord-649e19fc45a4436093d1782ff4aea1cf
Source dataset
uspto-grants-1996_09
Patent number
US05556977

Reaction notes

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