1-Bromo-2,4-difluorobenzene → 3(2,4-Difluorophenyl)thiophene

HRID 3076

Reaction equation

HRID 3076 reaction equation
F[C:2]1[CH:3]=[C:4]([C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[CH:5]=[C:6](F)[C:7]=1[F:8].BrC1C=CC([F:22])=CC=1F.BrC1C=C(F)C(F)=C(F)C=1>>[F:22][C:5]1[CH:6]=[C:7]([F:8])[CH:2]=[CH:3][C:4]=1[C:10]1[CH:14]=[CH:13][S:12][CH:11]=1

Participants

4

Reactant 3

HCID 676741-Bromo-2,4-difluorobenzeneHCID 6114091-Bromo-3,4,5-trifluorobenzeneHCID 232955283-(3,4,5-Trifluorophenyl)thiophene

Product 1

HCID 227436923(2,4-Difluorophenyl)thiopheneYield 97%

Conditions

Temperature
80 °C

Procedure

The same procedures set forth above in Example (1)(a) for synthesizing 3(3,4,5-trifluorophenyl)thiophene were followed, with the exception that 1-bromo-2,4-difluorobenzene was substituted for 1-bromo-3,4,5-trifluorobenzene as the 1-bromo-substituted fluorobenzene, and the coupling reaction mixture was heated to reflux in an oil bath for 10 hours with stirring at 80° C. (as opposed to being heated in an oil bath for 0.5 hour with periodically stirring). No further purification by recrystallization was required to obtain a 97 to 98% pure product.

Workup

  1. customthe coupling reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux in an oil bath for 10 hours
  4. temperatureto being heated in an oil bath for 0.5 hour
  5. stirringwith periodically stirring)
  6. customNo further purification
  7. customby recrystallization

Sources & evidence

ORD record
ord-84962d33083243bb8070accd1465b529
Source dataset
uspto-grants-1998_03
Patent number
US05733683

Linked notes

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