Benzene, 1-bromo-3-iodo- → 1-Bromo-3-isobutylbenzene

HRID 439409Notes

Reaction equation

HRID 439409 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[CH2:9]([Mg]Br)[CH:10]([CH3:12])[CH3:11]>C1C=CC=CC=1.O1CCCC1.O.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>[Br:8][C:4]1[CH:3]=[C:2]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 2

HCID 11561Benzene, 1-bromo-3-iodo-HCID 178418816HCID 178418816, compound

Product 1

HCID 187549911-Bromo-3-isobutylbenzene

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-iodo-3-bromobenzene (6.0 g, 21.2 mmol) in 100 mL of benzene at room temperature under argon, 1.2 g (1.06 mmol) of tetrakis(triphenylphosphine)palladium(0) was added and to this mixture a 2M solution in tetrahydrofuran of isobutyl magnesium bromide (10.6 mL) was added dropwise over 15 minutes. The mixture was stirred 2 hours, diluted with 100 mL of water, the organic layer was separated and the aqueous layer was extracted with 2×100 mL of ether. The combined organic extracts were dried and evaporated to provide 4.3 g of a colorless liquid, which upon distillation in vacuo provided 1.95 g (43%) of compound A as a colorless liquid; b.p. 124°-125° C. (15-20 mm).

Workup

  1. additionwas added dropwise over 15 minutes
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with 2×100 mL of ether
  4. customThe combined organic extracts were dried
  5. customevaporated

Sources & evidence

ORD record
ord-b8800b0816e34bc293b98ac63f6a94f8
Source dataset
uspto-grants-1996_05
Patent number
US05514696

Reaction notes

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