N-Bromosuccinamide → 5-(5-Bromooxazol-2-yl)-2-isopropoxybenzonitrile

HRID 1053753Notes

Reaction equation

HRID 1053753 reaction equation
[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([O:14][CH:15]([CH3:17])[CH3:16])=[C:10]([CH:13]=1)[C:11]#[N:12].[Br:18]NC(=O)CCC(N)=O>C(Cl)(Cl)(Cl)Cl>[Br:18][C:5]1[O:1][C:2]([C:6]2[CH:7]=[CH:8][C:9]([O:14][CH:15]([CH3:17])[CH3:16])=[C:10]([CH:13]=2)[C:11]#[N:12])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 9834204N-BromosuccinamideHCID 583549695-(4,5-Dihydrooxazol-2-yl)-2-isopropoxybenzonitrile

Product 1

HCID 583549795-(5-Bromooxazol-2-yl)-2-isopropoxybenzonitrileYield 55%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A stirring solution of 5-(4,5-dihydrooxazol-2-yl)-2-isopropoxybenzonitrile INT-31 (420 mg, 1.82 mmol), N-bromosuccinamide (990 mg, 5.56 mmol) and azoisobutyronitrile (14.9 mg, 0.09 mmol) in carbon tetrachloride (20 mL) was heated at 80° C. under N2 for 18 h. The reaction mixture was cooled to room temperature and the solids were removed by filtration. The filtrate was washed with sodium thiosulfate (20 mL) and brine (20 mL), and dried over MgSO4. The product was purified by chromatography (EA/hexanes) to afford 300 mg (55%) of 5-(5-bromooxazol-2-yl)-2-isopropoxybenzonitrile INT-32 as a yellow solid. LCMS-ESI (m/z) calculated for C13H11BrN2O2: 307.1; found 309.0 [M+2]+, tR=3.79 min. 1H NMR (400 MHz, CDCl3) δ 8.19-7.93 (m, 2H), 7.08-6.85 (m, 2H), 4.81-4.47 (m, 1H), 1.38 (dd, J=6.6, 3.0 Hz, 6H).

Workup

  1. customthe solids were removed by filtration
  2. washThe filtrate was washed with sodium thiosulfate (20 mL) and brine (20 mL)
  3. dry with materialdried over MgSO4
  4. customThe product was purified by chromatography (EA/hexanes)

Sources & evidence

ORD record
ord-5f21065e01934674a7d880859dc53e39
Source dataset
uspto-grants-2016_07
Patent number
US09394264B2

Reaction notes

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