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

HRID 1617230Notes

Reaction equation

HRID 1617230 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-7abccc1c5f6e4381a16595b303b6bfba
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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