Diisobutylaluminum hydride → 3-Bromo-4-iodobenzenemethanol

HRID 1961538Notes

Reaction equation

HRID 1961538 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[I:12])[C:5](OC)=[O:6].CC(C[AlH]CC(C)C)C>C(Cl)Cl.O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:9]=[CH:10][C:11]=1[I:12]

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 17750019Methyl 3-bromo-4-iodobenzoate

Product 1

HCID 166410803-Bromo-4-iodobenzenemethanolYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of methyl 3-bromo-4-iodobenzoate (Preparation 23, 4.3 g, 12.6 mmol) in CH2Cl2 was cooled, under N2, to −78° C. DIBAL-H was added slowly to the solution, which was stirred at −78° C. for 45 minutes and then allowed to come to room temperature. Next, the reaction mixture was diluted with 1M HCL (40 mL) and stirred for 30 minutes. The reaction was further diluted with water and extracted with CH2Cl2. The organic phase was dried (Na2SO4) and concentrated under vacuum to afford the intermediate (3.2 g, 82%) as a solid. 1HNMR (CDCl3): 7.85 (1H), 7.67 (1H), 7.02 (1H), 4.65 (2H), 1.76 (1H, OH).

Workup

  1. customto come to room temperature
  2. additionNext, the reaction mixture was diluted with 1M HCL (40 mL)
  3. stirringstirred for 30 minutes
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a06471d66edb4728870cc14b0610adc3
Source dataset
uspto-grants-2013_04
Patent number
US08415310B2

Reaction notes

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