Benzyl Bromide → HCID 67486384, compound

HRID 2371291Notes

Reaction equation

HRID 2371291 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH2:21]([O:13][C:12](=[O:14])[CH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 118343Benzeneacetic acid, 4-(1,1-dimethylethyl)-

Product 1

HCID 67486384HCID 67486384, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-tert-butyl-phenyl acetic acid (5.0 g, 26.04 mmol) in DMF (30 mL) at rt were added Cs2CO3 (12.72 g, 39.06 mmol) and benzyl bromide (4.89 g, 28.6 mmol). The reaction mixture was stirred for overnight at room temperature and then the reaction mixture was heated at 100° C. for 1 h and cool to rt. The solvent was removed under reduced pressure and poured into cold 1 N HCl (50 mL). The aqueous solution was extracted with ethyl acetate (2×100 mL) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure, dried under vacuum. (4-tert-butyl-phenyl)acetic acid benzyl ester was obtained as a yellowish liquid. (5.96 g, 81%): 1H NMR (300 MHz, CDCl3): δ 7.37-7.33 (m, 7H), 7.25 (dd, J=5.4, 13.2 Hz, 2H), 5.14 (s, 2H), 3.65 (s, 2H), 1.32 (s, 9H); TLC conditions: Uniplate silica gel, 250 microns; mobile phase=ethyl acetate-hexanes (1:5); Rf=0.8.

Workup

  1. temperaturethe reaction mixture was heated at 100° C. for 1 h
  2. temperaturecool to rt
  3. customThe solvent was removed under reduced pressure
  4. additionpoured into cold 1 N HCl (50 mL)
  5. extractionThe aqueous solution was extracted with ethyl acetate (2×100 mL)
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customdried under vacuum

Sources & evidence

ORD record
ord-f87eb71bf0bc49d184018fa1e6a2509a
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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