Azobisisobutyronitrile → 2-(3-(Bromomethyl)-4-methoxyphenyl)acetic acid

HRID 2387882Notes

Reaction equation

HRID 2387882 reaction equation
C1C(=O)N([Br:8])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([OH:32])=[O:31])=[CH:25][C:24]=1[CH3:33]>CCOC(C)=O>[Br:8][CH2:33][C:24]1[CH:25]=[C:26]([CH2:29][C:30]([OH:32])=[O:31])[CH:27]=[CH:28][C:23]=1[O:22][CH3:21]

Participants

5

Reactant 3

HCID 6547Azobisisobutyronitrile2×HCID 67184N-bromobutanimideHCID 1382764-Methoxy-3-methylphenylacetic acid

Product 1

HCID 671652482-(3-(Bromomethyl)-4-methoxyphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
80 °C

Procedure

NBS (2.72 g) and AIBN (0.136 g) were added in one portion to a solution of 2-(4-methoxy-3-methylphenyl)acetic acid (2.99 g) in EtOAc (50 ml) and stirred at 80° C. for 2 h. Another portion of AIBN (0.136 g) was added and the suspension stirred for a further 2 h. The reaction mixture was diluted with EtOAc, washed with sat. sodium thiosulfate solution, 2M HCl, water, and sat. brine. The organic phase was dried, filtered and evaporated to afford the subtitle compound, 4.10 g.

Workup

  1. stirringthe suspension stirred for a further 2 h
  2. washwashed with sat. sodium thiosulfate solution, 2M HCl, water, and sat. brine
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-1e9e8d72afe14ed3b52c6e8e7add6ccb
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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