Benzyl Bromide → 4-(Benzyloxy)-3-propylbenzonitrile

HRID 603383Notes

Reaction equation

HRID 603383 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][CH2:11][CH3:12].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[CH2:13]([O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][CH2:11][CH3:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 139876694-hydroxy-3-propylBenzonitrile

Product 1

HCID 670187734-(Benzyloxy)-3-propylbenzonitrileYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-3-propylbenzonitrile (0.97 g, 6 mmol) (Example 29) in DMF (20 mL) were added 10 drops of water, benzyl bromide (2.05 g, 12 mmol), and Cs2CO3 (2.93 g, 9 mmol), and the mixture was stirred for 12 h at rt. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in EtOAc and filtered. The precipitate was washed with more EtOAc. The combined filtrates were concentrated and purified by silica gel chromatography (EtOAc/hexanes (v/v)=1:19) to give 1.23 g (82%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 7.48-7.32 (m, 7H), 6.92 (d, 1H), 5.13 (s, 2H), 2.67 (t, 2H), 1.72-1.60 (m, 2H), 0.98 (t, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationfiltered
  3. washThe precipitate was washed with more EtOAc
  4. concentrationThe combined filtrates were concentrated
  5. custompurified by silica gel chromatography (EtOAc/hexanes (v/v)=1:19)

Sources & evidence

ORD record
ord-716b1330267f4054a0e9e3bb6d5eb584
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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