Water → HCID 86669781, compound

HRID 2371255Notes

Reaction equation

HRID 2371255 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].C1C(=O)N([Br:22])C(=O)C1.CCOC(C)=O.O>C1C=CC=CC=1.CC(N=NC(C#N)(C)C)(C#N)C>[Br:22][CH:11]([C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=1)[C:12]([OH:14])=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 118343Benzeneacetic acid, 4-(1,1-dimethylethyl)-

Product 1

HCID 86669781HCID 86669781, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 241BenzeneSolvent

Conditions

Temperature
70 °C

Procedure

To a stirring solution of (4-tert-butyl-phenyl)-acetic acid (1.5 g, 7.8 mmol) in benzene (30 mL) at room temperature was added NBS (1.39 g, 7.8 mmol) and AIBN (15 mg, 0.08 mmol). The mixture was heated at 70° C. for 16 hrs, added EtOAc and water. The organic layer was collected and dried over Na2SO4, filtered and concentrated under reduced pressure to afford crude bromo-(4-tert-butyl-phenyl)-acetic acid as a light yellow solid (2.1 g, 99%): 1H NMR (300 MHz, DMSO-d6): 7.46 (m, 4H), 5.74 (s, 1H), 1.29 (s, 9H).

Workup

  1. customThe organic layer was collected
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6a2517db8b4e42d1907ac75893ebbf8c
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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