Ethyl 4-bromo-5-(3-chlorophenyl)furan-2-carboxylate → Ethyl 4,5-bis(3-chlorophenyl)furan-2-carboxylate

HRID 2190120Notes

Reaction equation

HRID 2190120 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16](C#N)[CH:15]=2)[CH:5]=[C:6](F)[CH:7]=1.BrC1C=C(C(OCC)=O)OC=1C1C=CC=C([Cl:39])C=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:39])[CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 58064772Ethyl 4-bromo-5-(3-chlorophenyl)furan-2-carboxylateHCID 58064795Ethyl 4-(3-chloro-5-fluorophenyl)-5-(3-cyanophenyl)furan-2-carboxylate

Product 1

HCID 58064774Ethyl 4,5-bis(3-chlorophenyl)furan-2-carboxylate

Procedure

The preparation of the title compound takes place in analogy to the synthesis of the compound from Example 11A starting with the compound from Example 5A. Extraction is carried out with dichloromethane and purification is by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient). 452 mg (34% of theory) of the title compound are obtained.

Workup

  1. extractionExtraction
  2. customis carried out with dichloromethane and purification

Sources & evidence

ORD record
ord-8fded2013afd4d1f818084ddb25f86df
Source dataset
uspto-grants-2012_12
Patent number
US08324268B2

Reaction notes

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