Azobisisobutyronitrile → 3-bromo-4-(bromomethyl)benzoic Acid

HRID 594068

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:31])C(=O)C1>FC(F)(F)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][Br:31])[C:5]([OH:7])=[O:6]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3-bromo-4-methylbenzoic acid (1.0 equiv.) and AIBN (0.05 equiv.) in trifluorotoluene (0.28 M) was added NBS (1.1 equiv.). The mixture was heated at 90° C. overnight. The reaction mixture was partitioned between EtOAc and H2O. The organic layer was washed with NaCl(sat.), dried over MgSO4, filtered, concentrated to yield 3-bromo-4-(bromomethyl)benzoic acid in 60% yield. LC/MS (m/z)=294.8 (MH+), Rt=0.80 min.

Workup

customThe reaction mixture was partitioned between EtOAc and H2O
washThe organic layer was washed with NaCl(sat.)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-a5833216af294f4aa238714c4ebbf9dd
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242969B2

Linked notes

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