Dibenzofuran → HCID 178469643, compound

HRID 1731797Notes

Reaction equation

HRID 1731797 reaction equation
[NH2:1][C:2]1[C:3]([F:10])=[C:4]([Br:9])[C:5]([F:8])=[CH:6][CH:7]=1.C([O:13][CH:14]=[C:15]([C:21](OCC)=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17])C.C1(OC2C=CC=CC=2)C=CC=CC=1.C1C2C3C=CC=CC=3OC=2C=CC=1>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[Br:9][C:4]1[C:3]([F:10])=[C:2]2[C:7]([C:14]([OH:13])=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:21]=[N:1]2)=[CH:6][C:5]=1[F:8]

Participants

6

Reactant 4

HCID 568DibenzofuranHCID 6871Diethyl (ethoxymethylene)malonateHCID 7583Diphenyl EtherHCID 137327463-Bromo-2,4-difluoroaniline

Product 1

HCID 178469643HCID 178469643, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Conditions

Temperature
150 °C

Procedure

A stirred mixture of 26 g of 3-amino-2,6-difluorobromobenzene and 27 g of diethyl ethoxymethylenemalonate was heated at 150° C. for 1 hour. After cooling, 100 ml of Dowtherm "A" (commercially available high boiling inert solvent mixture of diphenylether and dibenzofuran) was added and the mixture was heated under nitrogen at 260° C. for 1.5 hour. The mixture was cooled to room temperature and 200 ml of hexanes was added. The resulting precipitate was collected by filtration, washed with hexanes and dried to give a cream solid, m.p. 285° C., yield 78% (32.32 g).

Workup

  1. temperatureAfter cooling
  2. additionwas added
  3. temperaturethe mixture was heated under nitrogen at 260° C. for 1.5 hour
  4. temperatureThe mixture was cooled to room temperature
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with hexanes
  7. customdried
  8. customto give a cream solid, m.p. 285° C., yield 78% (32.32 g)

Sources & evidence

ORD record
ord-f525477d456b41298c82e26a28c83bd3
Source dataset
uspto-grants-1986_11
Patent number
US04623650

Reaction notes

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