Hydrochloric Acid → (4-Bromo-6-fluoro-1h-indol-2-yl)methanol

HRID 857395Notes

Reaction equation

HRID 857395 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12](OC)=[O:13])[NH:6]2.[H-].C([Al+]CC(C)C)C(C)C.Cl>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH2:12][OH:13])[NH:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 21867463Methyl 4-bromo-6-fluoro-1H-indole-2-carboxylate

Product 1

HCID 21867424(4-Bromo-6-fluoro-1h-indol-2-yl)methanolYield 96.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of methyl 4-bromo-6-fluoro-1H-indole-2-carboxylate (3 g, 11 mmol) in THF (50 mL) at −30° C. was added diisobutylaluminum hydride (33 mmol, 1.5M toluene solution). The mixture was stirred for 1 hour at −30° C. and 1N HCl was added. The phases were separated and the aqueous layer was extracted with Et2O. The combined organic layers were dried over Na2SO4 and concentrated to give 2.6 g of the title compound used as such.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with Et2O
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-62c19ebd538d4c77bd4a41527a3c3744
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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