1-Bromoheptane → Heptylbenzene

HRID 1645704

Reaction equation

HRID 1645704 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[C:9]1([Mg]Cl)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1([B-](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([PH+](C(C)(C)C)C)(C)(C)C.O1CCCC1>[C:9]1([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 3

HCID 123691-BromoheptaneHCID 25517Ammonium ChlorideHCID 178478979HCID 178478979, compound

Product 1

HCID 14115Heptylbenzene

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 23136641Di-tert-butyl(methyl)phosphanium tetraphenylborate(1-)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A 50-ml four-necked flask was equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser. 0.045 g (0.2 mmol) of palladium (II) acetate and 2 ml of tetrahydrofuran were weighed in the flask, followed by stirring. Further, 0.096 g (0.2 mmol) of di-tert-butylmethylphosphonium tetraphenylborate obtained in Example B-1 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 22° C. for 30 minutes. 3.582 g (20 mmol) of n-heptyl bromide was added, followed by stirring at 22° C. for 30 minutes. 10 ml (22 mmol) of 2.2M tetrahydrofuran solution of phenylmagnesium chloride was added dropwise at 30° C. over a period of 10 minutes, followed by stirring at 30° C. for 3 hours. After the completion of the reaction, 10 ml of saturated aqueous ammonium chloride solution was added, followed by separation. The organic phase was purified by column chromatography to afford 2.997 g of 1-phenylheptane (yield: 85 mol % based on n-heptyl bromide). The identification of the product was made by mass spectroscopy.

Workup

  1. customA 50-ml four-necked flask was equipped with a stirrer
  2. additionadded into the flask
  3. customThe flask was purged with argon
  4. stirringby stirring at 22° C. for 30 minutes
  5. stirringby stirring at 22° C. for 30 minutes
  6. stirringby stirring at 30° C. for 3 hours
  7. additionwas added
  8. customfollowed by separation
  9. customThe organic phase was purified by column chromatography

Sources & evidence

ORD record
ord-01e64ed202f44a3cb4583dbb579cbddc
Source dataset
uspto-grants-2012_02
Patent number
US08124809B2

Linked notes

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