Dimethylformamide → (2-Bromo-5-iodophenyl)methanol

HRID 1041928Notes

Reaction equation

HRID 1041928 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:9]=1[C:10](O)=[O:11].CN(C=O)C>C(Cl)Cl>[Br:7][C:8]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:9]=1[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27355722-Bromo-5-iodobenzoic acid

Product 1

HCID 53424372(2-Bromo-5-iodophenyl)methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (13.0 mL) is added to an ice-cold solution of 2-bromo-5-iodo-benzoic acid in CH2Cl2 (200 mL). DMF (0.2 mL) is added and the solution is stirred at room temperature for 6 h. Then, the solution is concentrated under reduced pressure and the residue is dissolved in THF (100 mL). The resulting solution is cooled in an ice-bath and LiBH4 (3.4 g) is added in portions. The cooling bath is removed and the mixture is stirred at room temperature for 1 h. The reaction mixture is diluted with THF and treated with 0.1 M hydrochloric acid. Then, the organic layer is separated and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried (Na2SO4) and the solvent is evaporated under reduced pressure to give the crude product.

Workup

  1. concentrationThen, the solution is concentrated under reduced pressure
  2. dissolutionthe residue is dissolved in THF (100 mL)
  3. temperatureThe resulting solution is cooled in an ice-bath
  4. additionLiBH4 (3.4 g) is added in portions
  5. customThe cooling bath is removed
  6. stirringthe mixture is stirred at room temperature for 1 h
  7. additionThe reaction mixture is diluted with THF
  8. additiontreated with 0.1 M hydrochloric acid
  9. customThen, the organic layer is separated
  10. extractionthe aqueous layer is extracted with ethyl acetate
  11. dry with materialThe combined organic layers are dried (Na2SO4)
  12. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-d1edf4a6421e46c9baa35d19fc06abf7
Source dataset
uspto-grants-2013_10
Patent number
US08557782B2

Reaction notes

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