Triethylamine → 2-Diphenylphosphinobenzaldehyde

HRID 1883307Notes

Reaction equation

HRID 1883307 reaction equation
C(N(CC)CC)C.Br[C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12].[C:17]1([PH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:24]1([P:23]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[CH:11]=[O:12])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 70017DiphenylphosphineHCID 811292-Bromobenzaldehyde

Product 1

HCID 27543162-Diphenylphosphinobenzaldehyde

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

After 5.9 ml of triethylamine (43 mmol) and 334 mg of tetrakis(triphenylphosphine)palladium have been added, 5 ml of 2-bromobenzaldehyde (43 mmol) and 11.15 ml of diphenylphosphine (64.5 mmol) are refluxed in 150 ml of absolute toluene under a protective gas atmosphere in a three-necked flask equipped with a reflux condenser. Triethylamine hydrobromide precipitates as a white solid over the course of the reaction. After 12 hours, the reaction solution is filtered, washed three times with saturated ammonium hydrochloride solution and saturated sodium chloride solution and the solvent is removed in a rotary evaporator. The resultant crude product is recrystallised from methanol. Yield 10.61 g (85% of theoretical).

Workup

  1. customequipped with a reflux condenser
  2. customTriethylamine hydrobromide precipitates as a white solid over the course of the reaction
  3. filtrationthe reaction solution is filtered
  4. washwashed three times with saturated ammonium hydrochloride solution and saturated sodium chloride solution
  5. customthe solvent is removed in a rotary evaporator
  6. customThe resultant crude product is recrystallised from methanol

Sources & evidence

ORD record
ord-938204aa5b2f4298839f3172a7d34327
Source dataset
uspto-grants-2004_07
Patent number
US06759559B2

Reaction notes

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