Phosphorus tribromide → 2-Bromomethyl-4-methoxy-3-methyl benzofuran-5-carbonitrile

HRID 29467Notes

Reaction equation

HRID 29467 reaction equation
O[CH2:2][C:3]1[O:4][C:5]2[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([O:15][CH3:16])[C:6]=2[C:7]=1[CH3:8].P(Br)(Br)[Br:18]>ClCCl.N1C=CC=CC=1>[Br:18][CH2:2][C:3]1[O:4][C:5]2[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([O:15][CH3:16])[C:6]=2[C:7]=1[CH3:8]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 68713008HCID 68713008, compound

Product 1

HCID 687140752-Bromomethyl-4-methoxy-3-methyl benzofuran-5-carbonitrileYield 95%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-hydroxymethyl-4-methoxy-3-methyl benzofuran-5-carbonitrile (0.17 g; 0.76 mmol) in dichloromethane (5 mL) was cooled to 0° C. To this solution was added, successively, neat phosphorus tribromide (0.11 mL; 0.32 g; 1.2 mmol; 1.5 eq) and pyridine (2 drops). The ice bath was removed and the reaction was allowed to come to room temperature overnight with stirring. After quenching with ice, the crude product was isolated by ethyl acetate extraction. The organic layer was washed with saturated sodium bicarbonate, then dried over magnesium sulfate, filtered and concentrated in vacuo to give 2-bromomethyl-4-methoxy-3-methyl benzofuran-5-carbonitrile (0.20 g; 95% yield).

Workup

  1. additionTo this solution was added
  2. customThe ice bath was removed
  3. customAfter quenching with ice
  4. customthe crude product was isolated by ethyl acetate extraction
  5. washThe organic layer was washed with saturated sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae63625626194366aabe65ec0b0f2719
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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