Dimethylformamide → 4-Difluoro methoxy-8-nitro-1-formyl dibenzo[b,d]furan

HRID 2039660Notes

Reaction equation

HRID 2039660 reaction equation
Br[C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH:14]([F:16])[F:15])[CH:8]=[O:9].C([O-])(=O)C.[Na+].CN(C)C=O>>[F:15][CH:14]([F:16])[O:13][C:12]1[C:5]2[O:4][C:3]3[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:2]=3[C:6]=2[C:7]([CH:8]=[O:9])=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 247582824-Difluoromethoxy-3-(4-nitro-2-bromophenoxy)benzaldehyde

Product 1

HCID 211057104-Difluoro methoxy-8-nitro-1-formyl dibenzo[b,d]furanYield 73.3%

Procedure

To a mixture of 3-(2-bromo-4-nitrophenoxy)-4-(difluoromethoxy)benzaldehyde (11.5 g, 0.030 mol) and sodium acetate (3.7 g, 0.045 mol) in dimethylformamide (50 mL) palladium(II) acetate (0.68 g, 0.003 mol) was added in 4 different lots with 1 hour duration at 120-125° C. After the completion of the addition, it was refluxed for 16 hours. The reaction mixture was filtered through hyflo, washed with dimethylformamide (10 mL). The filtrate was poured into the cold water. The solid separated out was filtered. The solid was washed with hexane and dried. Yield—73.3%. HPLC (purity): 84.5%; Rf—0.5 (Ethyl acetate:Hexane (3:7)

Workup

  1. additionwas added in 4 different lots with 1 hour duration at 120-125° C
  2. additionAfter the completion of the addition, it
  3. temperaturewas refluxed for 16 hours
  4. filtrationThe reaction mixture was filtered through hyflo
  5. washwashed with dimethylformamide (10 mL)
  6. additionThe filtrate was poured into the cold water
  7. customThe solid separated out
  8. filtrationwas filtered
  9. washThe solid was washed with hexane
  10. customdried

Sources & evidence

ORD record
ord-e52a30bfcae64afbb41a65f52481ab92
Source dataset
uspto-grants-2013_11
Patent number
US08580795B2

Reaction notes

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