Isopropyl iodide → 2-Bromo-5-isopropoxybenzonitrile

HRID 1908108Notes

Reaction equation

HRID 1908108 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[K+].[K+].I[CH:18]([CH3:20])[CH3:19]>CN(C=O)C.CCOCC>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH:18]([CH3:20])[CH3:19])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 153231112-Bromo-5-hydroxybenzonitrile

Product 1

HCID 585508282-Bromo-5-isopropoxybenzonitrileYield 81%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Bromo-5-hydroxy-benzonitrile (20.0 g, 10.1 mmol) and K2CO3 (5.60 g, 40.4 mmol) were taken-up in dry DMF (12.5 mL). 2-Iodopropane (2.00 mL, 20.2 mmol) was added and the reaction mixture was heated at 60° C. for 2 h. The mixture was diluted with ether (100 mL), filtered over celite and the filtrate was washed with water (3×50 mL) and brine (50 mL), dried over MgSO4, evaporated and purified by column chromatography (5-45% EtOAc/hexanes) to give 1.9 g (81%) of 2-bromo-5-isopropoxybenzonitrile as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.53 (d, J=9.0 Hz, 1H), 7.15 (d, J=2.9 Hz, 1H), 6.99 (dd, J=9.0, 3.0 Hz, 1H), 4.58-4.49 (m, 1H), 1.36 (d, J=6.0 Hz, 6H). ESI-MS m/z calc. 239.0. found 240.1 (M+1)+. Retention time: 1.81 minutes (3 min run).

Workup

  1. filtrationfiltered over celite
  2. washthe filtrate was washed with water (3×50 mL) and brine (50 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. custompurified by column chromatography (5-45% EtOAc/hexanes)

Sources & evidence

ORD record
ord-bc85e63bf2474ea5b0abf140fd604501
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

Loading…