Hydrochloric Acid → (3-Bromo-6-chloro-2-fluorophenyl)methanol

HRID 2235185Notes

Reaction equation

HRID 2235185 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[C:9]([F:17])=[C:10]([C:13]([Cl:16])=[CH:14][CH:15]=1)[CH:11]=[O:12].O.Cl>C1COCC1>[Br:7][C:8]1[C:9]([F:17])=[C:10]([CH2:11][OH:12])[C:13]([Cl:16])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 592994573-Bromo-6-chloro-2-fluorobenzaldehyde

Product 1

HCID 59299314(3-Bromo-6-chloro-2-fluorophenyl)methanolYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add 1M LAH in THF (20 mL, 20 mmol) to 3-bromo-6-chloro-2-fluoro-benzaldehyde (Preparation 7) (4.9 g, 20 mmol) in THF (20 mL) at −78° C. Stir for 15 minutes and warm up to room temperature. Add reaction mixture into ice and water. Add 1M HCl (5 mL, 5 mmol) to dissolve the solid. Extract the mixture with ethyl acetate (50 mL), dry with magnesium sulfate, filter and evaporate solvent under reduced pressure to obtain 4.6 g (94%) of the title compound as a white solid.

Workup

  1. additionAdd
  2. dissolutionto dissolve the solid
  3. extractionExtract the mixture with ethyl acetate (50 mL)
  4. dry with materialdry with magnesium sulfate
  5. filtrationfilter
  6. customevaporate solvent under reduced pressure

Sources & evidence

ORD record
ord-c046f86761124b0ba81c66ef5ae57935
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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