3-Bromo-4-methoxybenzaldehyde → 5-Formyl-2-methoxybenzonitrile

HRID 1161051Notes

Reaction equation

HRID 1161051 reaction equation
[Cu][C:2]#[N:3].Br[C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH:8]=[O:9]>CN(C)C=O>[CH:8]([C:7]1[CH:6]=[CH:5][C:12]([O:13][CH3:14])=[C:11]([CH:10]=1)[C:2]#[N:3])=[O:9]

Participants

4

Reactant 2

HCID 986623-Bromo-4-methoxybenzaldehydeHCID 178418546HCID 178418546, compound

Product 1

HCID 226207855-Formyl-2-methoxybenzonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Add copper (I) cyanide (4.58 g, 51.2 mmol) to a solution of 3-bromo-4-methoxy-benzaldehyde (10.0 g, 46.5 mmol) in N,N-dimethylformamide (0.2 M). Heat the solution to 120° C. and stir the solution for 1 d. Quench with potassium carbonate (sat) and extract with diethyl ether (5×). Wash organic layers with water, dry with sodium sulfate, and concentrate to afford the title compound (5.00 g, 31.0 mmol, 67%): 1H NMR (400 MHz, DMSO-d6) δ 4.04 (s, 3H), 7.47 (d, J=8.6 Hz, 1H), 8.20 (m, 1H), 8.33 (m, 1H), 9.91 (s, 1H).

Workup

  1. customQuench with potassium carbonate (sat)
  2. extractionextract with diethyl ether (5×)
  3. dry with materialWash organic layers with water, dry with sodium sulfate
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-29ec6591f3b74b6ab0bb105372502a78
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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