N-bromobutanimide → Methyl 3-(3-bromo-4-hydroxyphenyl)propanoate

HRID 1865041Notes

Reaction equation

HRID 1865041 reaction equation
[H+].[B-](F)(F)(F)F.CCOCC.[CH3:12][O:13][C:14](=[O:24])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.[Br:25]N1C(=O)CCC1=O.OS([O-])(=O)=O.[Na+]>C(#N)C>[CH3:12][O:13][C:14](=[O:24])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([Br:25])[CH:18]=1

Participants

6

Reactant 4

HCID 67184N-bromobutanimideHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 516919Sodium BisulfateHCID 16211330Borate(1-), tetrafluoro-, hydrogen, compd. with 1,1'-oxybis(ethane) (1:1:1)

Product 1

HCID 22558720Methyl 3-(3-bromo-4-hydroxyphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Add HBF4-Et2O (4.4 mL, 27.7 mmol) to methyl-3-(4-hydroxyphenyl)-propionate (5.0 g, 27.7 mmol) in acetonitrile with stirring at 0° C. After 10 minutes, add N-bromosuccinimide (5.4 g, 30.5 mmol) and gradually allow to warm to room temperature. After 18 hours, pour into 38% NaHSO4 and extract with diethyl ether. Combine the organic extracts, wash with water and brine, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure to provide the title compound.

Workup

  1. temperatureto warm to room temperature
  2. waitAfter 18 hours
  3. extractionextract with diethyl ether
  4. washwash with water and brine
  5. dry with materialdry over anhydrous magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-4fdcd1bb29cf48329863fc6ab830983a
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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