1-Bromopropane → 1-Bromo-4-propylbenzene

HRID 234382

Reaction equation

HRID 234382 reaction equation
[Br:1][CH2:2][CH2:3][CH3:4].[Mg].I[C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1>O1CCCC1.C1C=CC=CC=1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[CH:12]=[CH:7][C:8]([CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 78401-BromopropaneHCID 115221-Bromo-4-iodobenzeneHCID 5462224Magnesium

Product 1

HCID 1363741-Bromo-4-propylbenzeneYield 1,414.8%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-bromopropane (1.32 g, 0.6 mmol) was added dropwise at room temperature at a rate such that a gentle reflux was maintained to a suspension of magnesium (258 mg, 12 mmol) in dry tetrahydrofuran. The cloudy suspension was stored at room temperature for an additional 30 minutes to produce a gray solution that was then added dropwise over 15 minutes to a mixture of 1-iodo-4-bromobenzene (3.0 g, 10.6 mmol) and tetrakis (triphenylphosphine) palladium (0) in 50 mL of dry benzene at room temperature. The mixture was stirred for 2 hours, diluted with 50 mL of water, the organic layer was separated and the aqueous layer was extracted with ether (2×50 mL). The combined organic extracts was dried and evaporated to yield 1.69 g (80%) of a light brown oil, which was used in the next step without further purification.

Workup

  1. temperaturea gentle reflux
  2. customto produce a gray solution that
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with ether (2×50 mL)
  5. customThe combined organic extracts was dried
  6. customevaporated

Sources & evidence

ORD record
ord-b3383e7d669a452f87c1719f45c9bde1
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Linked notes

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