Toluene → 5-Bromobenzofuran-2-carboxylic Acid Diethylamide

HRID 1860623Notes

Reaction equation

HRID 1860623 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](Cl)=[O:11])=[CH:7][C:6]=2[CH:13]=1.[CH2:14]([N:16](C(C)C)[CH:17](C)[CH3:18])[CH3:15].C1(C)C=CC=CC=1.C(NCC)C>O>[CH2:14]([N:16]([CH2:17][CH3:18])[C:10]([C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:13][C:6]=2[CH:7]=1)=[O:11])[CH3:15]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 27955345-Bromobenzo[b]furan-2-carbonyl chloride

Product 1

HCID 99481065-Bromobenzofuran-2-carboxylic Acid DiethylamideYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.3 g. of 5-bromobenzofuran-2-carbonyl chloride, 1 mL [sic] of ethyldiisopropylamine and 30 mL [sic] of toluene are mixed and 0.62 ml of diethylamine is added to the brown-coloured solution with stirring. A precipitate is formed with a slightly exothermic reaction. After 5 minutes, the mixture was treated with 30 ml of completely deionized water and the phases were separated. The organic phase was washed with 1.) 20 ml of iN HCl 2.) 20 ml of iN NaOH 3.) 20 ml of water and then with 20 ml of saturated NaCl solution and then freed of solvent components in vacuo. After chromatography on silica gel the residual, yellowish oil forms in the eluent MtB ether/heptane 2:1 [sic]. Final weight: 1.3 g of colourless crystals [sic] (yield: 88%), m.p. 79-81°.

Workup

  1. customA precipitate is formed with a slightly exothermic reaction
  2. customthe phases were separated
  3. washThe organic phase was washed with 1

Sources & evidence

ORD record
ord-e9a61a07ea404af9b3049a840a309c3b
Source dataset
uspto-grants-2003_03
Patent number
US06531503B1

Reaction notes

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