N-bromobutanimide → 2-(3-(Bromomethyl)-4-methoxyphenyl)acetic acid

HRID 553295

Reaction equation

HRID 553295 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][C:12]=1[CH3:21]>C(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:1][CH2:21][C:12]1[CH:13]=[C:14]([CH2:17][C:18]([OH:20])=[O:19])[CH:15]=[CH:16][C:11]=1[O:10][CH3:9]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1382764-Methoxy-3-methylphenylacetic acid

Product 1

HCID 671652482-(3-(Bromomethyl)-4-methoxyphenyl)acetic acidYield 96.2%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 6212ChloroformSolvent

Procedure

N-Bromosuccinimide (1.0 g) and 2,2′-azobis(2-methylpropionitrile) (20 mg) were added to a solution of (4-methoxy-3-methyl-phenyl)-acetic acid (1.1 g) in chloroform (25 mL) and heated to reflux for 4 hours. On cooling, the mixture was evaporated, the residue dissolved in ethyl acetate, washed sequentially with 2M aqueous hydrochloric acid (2×50 mL), brine (50 mL), dried (magnesium sulfate) and concentrated to give the subtitle compound as an oil (1.4 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. temperatureOn cooling
  4. customthe mixture was evaporated
  5. dissolutionthe residue dissolved in ethyl acetate
  6. washwashed sequentially with 2M aqueous hydrochloric acid (2×50 mL), brine (50 mL)
  7. dry with materialdried (magnesium sulfate)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8d9af2899a0c4e54b61b9d2a76179eb2
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Linked notes

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