5-Chloro-2-iodobenzoic acid → (5-Chloro-2-iodophenyl)methanol

HRID 869055Notes

Reaction equation

HRID 869055 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH2:7][OH:8])[CH:10]=1

Participants

3

Reactant 1

HCID 1394515-Chloro-2-iodobenzoic acid

Product 1

HCID 818020(5-Chloro-2-iodophenyl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-dimethylsulfide complex (3.7 mL, 38.9 mmol) was added slowly to a cold (0° C.) solution of 5-chloro-2-iodo-benzoic acid (10 g, 35.4 mmol) in THF (20 mL). The reaction mixture was allowed to warm to rt, stirred for 8 h, quenched by addition of a saturated aqueous solution of ammonium chloride, and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered, and concentrated to provide 9.5 g of the title compound. tR: 4.72 min (HPLC 2); Rf=0.66 (hexane/EtOAc, 7:3).

Workup

  1. customquenched by addition of a saturated aqueous solution of ammonium chloride
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c82568cc872847eaa2af41f55dc5df2a
Source dataset
uspto-grants-2015_03
Patent number
US08969341B2

Reaction notes

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