N-bromobutanimide → 3-[(2-Amino-3-bromo-6-fluoro-5-methylphenyl)oxy]-5-chlorobenzonitrile

HRID 1875176Notes

Reaction equation

HRID 1875176 reaction equation
[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([Cl:17])[CH:16]=2)[C:12]#[N:13])=[C:6]([F:18])[C:5]([CH3:19])=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].C1C(=O)N([Br:32])C(=O)C1>C(#N)C>[NH2:1][C:2]1[C:3]([Br:32])=[CH:4][C:5]([CH3:19])=[C:6]([F:18])[C:7]=1[O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([Cl:17])[CH:16]=1)[C:12]#[N:13]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 517165Ammonium AcetateHCID 594516283-[(6-Amino-2-fluoro-3-methylphenyl)oxy]-5-chlorobenzonitrile

Product 1

HCID 866449443-[(2-Amino-3-bromo-6-fluoro-5-methylphenyl)oxy]-5-chlorobenzonitrileYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-[(6-amino-2-fluoro-3-methylphenyl)oxy]-5-chlorobenzonitrile (7.422 g, 26.8 mmol) and ammonium acetate (0.207 g, 2.68 mmol) in acetonitrile (150 ml) was added NBS (5.01 g, 28.2 mmol) and the reaction mixture was stirred for two hours at rt. The solvent was removed and the crude material was purified via silica gel chromatography to give 3-[(2-amino-3-bromo-6-fluoro-5-methylphenyl)oxy]-5-chlorobenzonitrile (8.379 g, 23.56 mmol, 88% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.71 (s, 1H), 7.33 (s, 1H), 7.23-7.30 (m, 2H), 5.31 (s, 2H), 2.08 (s, 3 H).

Workup

  1. customThe solvent was removed
  2. customthe crude material was purified via silica gel chromatography

Sources & evidence

ORD record
ord-7290039fd1c7488ca87cd4163e99ab5c
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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