Formamide → 5-Bromobenzofuran-2-carboxamide

HRID 1883947Notes

Reaction equation

HRID 1883947 reaction equation
Br[CH2:2][C:3]([O:5]CC)=O.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([OH:17])=[C:13]([CH:16]=1)[CH:14]=O.C(=O)([O-])[O-].[K+].[K+].C([NH2:26])=O.C[O-].[Na+]>CN1C(=O)CCC1.O>[Br:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][C:2]([C:3]([NH2:26])=[O:5])=[CH:14][C:13]=2[CH:16]=1

Participants

8

Reactant 5

HCID 713FormamideHCID 7748Ethyl bromoacetate2×HCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 25026635-Bromobenzofuran-2-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Performance of the reaction with ethyl bromoacetate: 200 g of 5-bromo-2-hydroxybenzaldehyde are dissolved in 2000 ml of NMP with stirring, and 144 g of potassium carbonate and 175 g of ethyl bromoacetate are added. The mixture is stirred at 105° under nitrogen for 15 hours. The resultant orange solution dotted with crystals is cooled to 25°, 135 g of formamide are added, and the mixture is stirred for a further 30 minutes. 557 ml of sodium methoxide (30% in MeOH) are then allowed to run in over the course of 15 minutes without cooling. After 3 hours, a brownish solution dotted with crystals is present. It is poured into 6 litres of demineralized water (10°), and the mixture is stirred for a further 30 minutes. The crystals are filtered off with suction, washed with 1 litre of demineralized water, re-suspended in 4 litres of demineralized water, filtered off with suction and re-washed with 1 litre of demineralized water. The crystals are dried overnight to constant weight under reduced pressure at 60° C. (product weight: 113 g of pale beige crystals; m.p. 210-213°; CAS 35351-21-4).

Workup

  1. stirringThe mixture is stirred at 105° under nitrogen for 15 hours
  2. temperatureis cooled to 25°
  3. stirringthe mixture is stirred for a further 30 minutes
  4. customto run in over the course of 15 minutes
  5. temperaturewithout cooling
  6. stirringthe mixture is stirred for a further 30 minutes
  7. filtrationThe crystals are filtered off with suction
  8. washwashed with 1 litre of demineralized water
  9. filtrationfiltered off with suction
  10. washre-washed with 1 litre of demineralized water
  11. dry with materialThe crystals are dried overnight to constant weight under reduced pressure at 60° C. (product weight: 113 g of pale beige crystals; m.p. 210-213°; CAS 35351-21-4)

Sources & evidence

ORD record
ord-7feb1e1ae89d41ef890a92d8d916f4d9
Source dataset
uspto-grants-2004_07
Patent number
US06762300B2

Reaction notes

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