Water → HCID 44255054, compound

HRID 2220591Notes

Reaction equation

HRID 2220591 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][C:11]=3[CH:12]=2)[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=1.O>CN(C=O)C>[C:34]([C:33]1[CH:36]=[CH:37][C:30]([O:29][CH2:28][CH2:27][CH2:26][O:1][C:2]2[CH:3]=[C:4]([C:8]3[O:9][C:10]4[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][C:11]=4[CH:12]=3)[CH:5]=[CH:6][CH:7]=2)=[CH:31][CH:32]=1)#[N:35]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10879224HCID 10879224, compoundHCID 44254688HCID 44254688, compound

Product 1

HCID 44255054HCID 44255054, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(3-hydroxphenyl)-5-cyanobenzofuran (125) (1.176 g, 5 mmol) and K2CO3 (0.829 g, 6 mmol) in dry DMF (25 mL) was heated up to 60° C. 4-(3-Bromopropoxy)benzonitrile (129) was added in one portion and the reaction was kept at 80-100° C. overnight. The mixture was cooled down to room temperature and poured into iced water (100 mL) and stirred for 30 min. A precipitate formed was separated by filtration, washed with water (50 mL) and ethanol (50 mL). Drying under high vacuum and recrystallization from the mixture of DMF and ethanol afforded the desired product as white solid (1.65 g, 84%): mp 157-158° C. (DMF/EtOH). 1H NMR (DMSO-d6) δ8.24 (d, J=1.6 Hz, 1H), 7.86 (d, J=8.6 Hz, 1H), 7.78 (d, J=8.8 Hz, 2H), 7.77 (dd, J=8.6, 1.6 Hz, 1H), 7.61 (s, 1H), 7.55 (d, J=7.8 Hz, 1H), 7.52 (m, 1H), 7.45 (dd, J=7.8, 7.8 Hz, 1H), 7.16 (d, J=8.8 Hz, 2H), 7.07 (dd, J=7.8, 1.7 Hz, 1H), 4.35-4.15 (m, 4H), 2.30-2.15 (m, 2H). HPLC (method B) tR 9.63 min (100.0 area %). Anal. (C25H18N2O3) C, H, N.

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. customA precipitate formed
  3. customwas separated by filtration
  4. washwashed with water (50 mL) and ethanol (50 mL)
  5. dry with materialDrying under high vacuum and recrystallization from the mixture of DMF and ethanol

Sources & evidence

ORD record
ord-c041a1851e4d4c0396b1f39e1584128d
Source dataset
uspto-grants-2008_08
Patent number
US07417158B2

Reaction notes

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