Benzonitrile, 3-(bromomethyl)- → 3-(3-Cyanobenzyloxy)-5-(4-cyanophenoxy)benzoic acid ethyl ester

HRID 1024730Notes

Reaction equation

HRID 1024730 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Br)#[N:2].[CH2:11]([O:13][C:14](=[O:31])[C:15]1[CH:20]=[C:19]([OH:21])[CH:18]=[C:17]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[CH:16]=1)[CH3:12]>CN(C=O)C>[CH2:11]([O:13][C:14](=[O:31])[C:15]1[CH:16]=[C:17]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[CH:18]=[C:19]([O:21][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH:20]=1)[CH3:12]

Participants

4

Reactant 2

HCID 97249Benzonitrile, 3-(bromomethyl)-HCID 668184083-(4-Cyanophenoxy)-5-hydroxy benzoic acid ethyl ester

Product 1

HCID 668186143-(3-Cyanobenzyloxy)-5-(4-cyanophenoxy)benzoic acid ethyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium carbonate K2CO3 0.44 g (3.18 mmol) followed by 3-cyano benzylbromide 0.31 g (1.58 mmol) in 2 ml of DMF were added to a solution of 3-(4-cyano phenoxy)-5-hydroxy benzoic acid ethyl ester 0.45 g (1.58 mmol) in 7 ml of DMF at 20° C. The reaction mixture was allowed to attain RT and stirred overnight. The reaction mixture was quenched with ice cold water, extracted with ethyl acetate. The organic layer was washed with water followed by brine, dried over anhydrous sodium sulphate and concentrated to afford 0.51 g of a thick oily liquid. 1H NMR (CDCl3): δ 1.3 (3H, t), 4.3 (2H, q), 5.25 (2H, s), 6.88 (1H, s), 7.02 (2H, d), 7.34 (1H, s), 7.5 (2H, m), 7.66 (4H, m), 7.78 (1H, s).

Workup

  1. customto attain RT
  2. customThe reaction mixture was quenched with ice cold water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dcfdb0f2fee1408888b730641ba101e2
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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