Iodoethane → 1,3-Dibromo-2-ethylbenzene

HRID 76799

Reaction equation

HRID 76799 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[CH2:9](I)[CH3:10].[Li+].CC([N-]C(C)C)C.[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 79271,3-DibromobenzeneHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamide

Product 1

HCID 148478061,3-Dibromo-2-ethylbenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A three necked round-bottom flask was purged with argon and then filled with dry THF (1.2 l), 1,3-dibromo benzene (121 g, 0.514 mol) and ethyl iodide (95.4 g, 0.611 mol). The mixture was cooled to −78° C. and LDA (64.2 g, 0.697 mol) (2 M in THF/n-heptane/ethyl benzene) was added slowly in a way that the temperature did not rise above −65° C. After stirring for 2.75 h the reaction was poured onto 1 l sat. aq. NH4Cl solution and stirred vigorously for 20 min. Two times extraction with DCM yielded colorless oil (167 g) which was used in the next step without further purification.

Workup

  1. customA three necked round-bottom flask was purged with argon
  2. customdid not rise above −65° C
  3. stirringstirred vigorously for 20 min
  4. extractionTwo times extraction with DCM yielded colorless oil (167 g) which
  5. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-07d968876b81431686c441504a41308c
Source dataset
uspto-grants-2014_09
Patent number
US08835653B2

Linked notes

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