Acrylonitrile → 2H-1-Benzopyran-3-carbonitrile, 6-bromo-

HRID 1019678Notes

Reaction equation

HRID 1019678 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[CH:4]=O.[C:11](#[N:14])[CH:12]=[CH2:13].N12CCN(CC1)CC2>C(OCC)C>[Br:10][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[O:1][CH2:13][C:12]([C:11]#[N:14])=[CH:4]2

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 9237DabcoHCID 728635-Bromosalicylaldehyde

Product 1

HCID 424392H-1-Benzopyran-3-carbonitrile, 6-bromo-Yield 70.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-hydroxy-5-bromobenzaldehyde XXIX (30 g, 0.15 mol), acrylonitrile (50 g, 0.75 mol), and 1,4-diazabicyclo[2.2.2]octane (Dabco, 4 g, 0.035 mol) was refluxed overnight. The reaction mixture was diluted with ethyl ether and washed with NaOH (1N), water, HCl (1N) and brine. The organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo to give 25 g of 6-bromo-2H-chromene-3-carbonitrile XXX (Yield 70%). MS: calc'd 237 (MH+), exp 237 (MH+).

Workup

  1. temperaturewas refluxed overnight
  2. washwashed with NaOH (1N), water, HCl (1N) and brine
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-785134a95a424508bb2207270791be01
Source dataset
uspto-grants-2014_05
Patent number
US08716285B2

Reaction notes

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