Hydrochloric Acid → (5-Bromo-2-chlorophenyl)methanol

HRID 427251

Reaction equation

HRID 427251 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:12])=[C:6]([CH:11]=1)[C:7](OC)=[O:8].CC(C[AlH]CC(C)C)C.CCCCCC.Cl>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:12])=[C:6]([CH:11]=1)[CH2:7][OH:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 14487Diisobutylaluminum hydrideHCID 842098Methyl 5-bromo-2-chlorobenzoate

Product 1

HCID 5074766(5-Bromo-2-chlorophenyl)methanolYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

25.0 g of methyl 5-bromo-2-chlorobenzoate was dissolved in 130 ml of dichloromethane. To this solution, 230 ml of a 0.96 M DIBAL (diisobutylalminium hydride) hexane solution was added at −40° C. in a nitrogen atmosphere, followed by stirring at room temperature for 4 hours. To this reaction solution, 10% hydrochloric acid was carefully added while cooling, followed by extraction with ethyl acetate and drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained crude crystals were washed with hexane to obtain 20.8 g of 5-bromo-2-chlorobenzyl alcohol as white crystals.

Workup

  1. temperaturewhile cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe obtained crude crystals
  6. washwere washed with hexane

Sources & evidence

ORD record
ord-07e2e2f8419c4e1585ce0de5e3e8845e
Source dataset
uspto-grants-2001_11
Patent number
US06313071B1

Linked notes

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