Dimethylformamide → 6-Bromo-2,3-diphenylbenzofuran

HRID 1893107Notes

Reaction equation

HRID 1893107 reaction equation
[C:1]1([C:7]2[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:22]N1C(=O)CCC1=O.CN(C)C=O>O>[Br:22][C:13]1[CH:14]=[CH:15][C:9]2[C:8]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:11][C:10]=2[CH:12]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 253613Benzofurans

Product 1

HCID 598665016-Bromo-2,3-diphenylbenzofuranYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

43.2 g of 2,3-diphenylbenzo[b]furan, 31.3 g of N-bromosuccinimide, and 400 mL of N,N-dimethylformamide were loaded into a flask, and the mixture was stirred under heat at 70° C. for 8 hours. After having been cooled to room temperature, the reaction solution was poured into 2 L of water. The precipitated crystal was separated by filtration, washed with methanol, water, and methanol in the stated order, and purified by silica gel column chromatography, whereby 40.2 g of a pale yellow crystal were obtained (72% yield).

Workup

  1. temperatureAfter having been cooled to room temperature
  2. customThe precipitated crystal was separated by filtration
  3. washwashed with methanol, water, and methanol in the stated order
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-2efb7776e1714f52afeaba944ee9ad20
Source dataset
uspto-grants-2013_08
Patent number
US08512875B2

Reaction notes

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