Benzyl Bromide → HCID 66971842, compound

HRID 1361072Notes

Reaction equation

HRID 1361072 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:15]([O:19][C:20]1[CH:21]=[C:22]([CH2:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH:23]=[CH:24][C:25]=1[CH2:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([O:36][CH3:37])[CH:30]=1)[CH2:16][CH2:17][CH3:18]>C(C(C)=O)C.C(OCC)(=O)C>[CH2:7]([O:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][CH2:27][CH2:26][C:25]2[CH:24]=[CH:23][C:22]([CH2:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])=[CH:21][C:20]=2[O:19][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:30][C:31]=1[O:36][CH3:37])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 66971962HCID 66971962, compound

Product 1

HCID 66971842HCID 66971842, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

0.2 g (0.75 mmol) of potassium carbonate and then 0.2 ml (0.75 mmol) of benzyl bromide are added to a solution of 0.25 g (0.62 mmol) of methyl 3-{3-butoxy-4-[3-(4-hydroxy-3-methoxyphenyl)propyl]phenyl}propanoate in 25 ml of methyl ethyl ketone. The reaction mixture is heated at 70° C. for 24 hours and then cooled, diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with an 80/20 heptane/ethyl acetate mixture. 276 mg (93%) of methyl 3-{4-[3-(4-benzyloxy-3-methoxyphenyl)propyl]-3-butoxyphenyl}propanoate are obtained in the form of a colorless oil.

Workup

  1. temperaturecooled
  2. washwashed with saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with an 80/20 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-12c6af504bac445e81920f72556dbfd0
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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