Ethyl Acetate → HCID 68088310, compound

HRID 1503650Notes

Reaction equation

HRID 1503650 reaction equation
Br[C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][CH2:3]1.[Mg].[Br:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[C:25]#N.C(OCC)(=[O:32])C>O1CCCC1.O>[Br:21][C:22]1[CH:23]=[C:24]([C:25]([C:4]2[CH:3]=[C:2]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=2)=[O:32])[CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 233813-BromobenzonitrileHCID 5462224MagnesiumHCID 86667752HCID 86667752, compound

Product 1

HCID 68088310HCID 68088310, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

A solution of 20.0 g (64.7 mmol) of 3-bromo-[3,1′;5,1″]terphenyl in 300 ml of tetrahydrofuran is slowly added dropwise to 1.7 g (71.2 mmol) of magnesium turnings, and the mixture is heated under reflux for 3 h. The solution is then cooled to −40° C., and a solution of 11.8 g (65 mmol) of 3-bromobenzonitrile in 100 ml of tetrahydrofuran is added dropwise. After the addition, the solution is heated under reflux for 6 h. After cooling, 600 ml of ethyl acetate and 400 ml of water are added, and the organic phase is separated off, washed three times with 200 ml of water, dried using sodium sulfate and subsequently evaporated to dryness. The residue is recrystallised from ethanol and subsequently dried under reduced pressure. The yield is 21.7 g (53 mmol), corresponding to 81.3% of theory.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 3 h
  3. additionAfter the addition
  4. temperaturethe solution is heated
  5. temperatureunder reflux for 6 h
  6. temperatureAfter cooling
  7. customthe organic phase is separated off
  8. washwashed three times with 200 ml of water
  9. customdried
  10. customsubsequently evaporated to dryness
  11. customThe residue is recrystallised from ethanol
  12. customsubsequently dried under reduced pressure

Sources & evidence

ORD record
ord-46234f4c8cbd40d88b03e072a54a8f8d
Source dataset
uspto-grants-2015_12
Patent number
US09212198B2

Reaction notes

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