Hydrochloric Acid → 2-Chloro-5-iodobenzyl alcohol

HRID 602057Notes

Reaction equation

HRID 602057 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4](O)=[O:5].C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>CO>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140Toluene2×HCID 5196382-Chloro-5-iodobenzoic acidHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 671539432-Chloro-5-iodobenzyl alcoholYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-chloro-5-iodobenzoic acid (28 g, 99 mmoles) and toluene (198 mL) was cooled to 0° C. A 1M diisobutyl aluminium hydride (DIBAL) solution in toluene 208 mL, 208 mmol) solution was added drop wise over 20 minutes. The solution was allowed to slowly warm to rt. After 16 h the solution was cooled to 0° C., MeOH and 1M HCl was slowly added (exothermic reaction). The solution became clumpy and was filtered and the clumps washed with EtOAc. The organic phase was then isolated and the aqueous layer washed with EtOAc. The combined organic extracts were then washed with brine, dried (Na2SO4), and concentrated. The product was purified by Biotage chromatography (0%-100% EtOAc/Hexanes) to afford 9.01 g of product as a solid (34%). 1H NMR (400 MHz, chloroform-d) δ ppm 7.85 (d, J=2.02 Hz, 1 H) 7.55 (dd, J=8.34, 2.27 Hz, 1 H) 7.09 (d, J=8.34 Hz, 1 H) 4.74 (s, 2 H) 2.25 (s, 1 H).

Workup

  1. temperatureAfter 16 h the solution was cooled to 0° C.
  2. custom(exothermic reaction)
  3. filtrationwas filtered
  4. washthe clumps washed with EtOAc
  5. customThe organic phase was then isolated
  6. washthe aqueous layer washed with EtOAc
  7. washThe combined organic extracts were then washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe product was purified by Biotage chromatography (0%-100% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-ac638998e7b84954894bb41248054734
Source dataset
uspto-grants-2011_03
Patent number
US07902394B2

Reaction notes

Loading…