Methanol → Methyl 4-bromo-2,2-diphenylbutyrate

HRID 455903

Reaction equation

HRID 455903 reaction equation
[Br:1][CH2:2][CH2:3][C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:24]O>C(Cl)(Cl)Cl.CN(C)C=O>[CH3:24][O:6][C:5](=[O:7])[C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:3][CH2:2][Br:1]

Participants

6

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27569594-Bromo-2,2-diphenylbutyric acid

Product 1

HCID 22624494Methyl 4-bromo-2,2-diphenylbutyrate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

4-Bromo-2,2-diphenylbutyric acid (5.0 g, 16 mmol), thionyl chloride (1.1 mL, 16 mmol), and N,N-dimethylformamide (0.02 mL, 0.20 mmol) in chloroform (16 mL) were mixed at room temperature under a stream of nitrogen. The reaction mixture was heated to reflux, stirred under reflux for 4 h, and cooled to 0° C. Methanol (50 mL) was added. The reaction mixture was warmed to room temperature and concentrated to dryness, yielding a brown oil. The crude material was purified on SiO2 (120 g) using 10% EtOAc/Hexanes as eluent to provide the title compound (3.9 g) as a clear oil that crystallized on standing. 1H NMR (DMSO-d6, 400 mHz) δ (ppm): 7.33-7.20 (m, 10H), 3.70 (s, 3H), 3.12-3.08 (m, 2H), 2.98-2.93 (m, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperatureunder reflux for 4 h
  4. temperatureThe reaction mixture was warmed to room temperature
  5. concentrationconcentrated to dryness
  6. customyielding a brown oil
  7. customThe crude material was purified on SiO2 (120 g)

Sources & evidence

ORD record
ord-e6c8f398d1114b69b22f8cd8ed45779b
Source dataset
uspto-grants-2013_07
Patent number
US08497287B2

Linked notes

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