Ammonium Chloride → 1-(2-Bromo-6-fluoro-phenyl)-propan-1-ol

HRID 1392684Notes

Reaction equation

HRID 1392684 reaction equation
[CH3:1][CH2:2][Mg+].[Br-].[Br:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:7]=1[CH:8]=[O:9].[NH4+].[Cl-]>C1COCC1>[Br:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:7]=1[CH:8]([OH:9])[CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 224739772-Bromo-6-fluorobenzaldehydeHCID 178461630HCID 178461630, compound

Product 1

HCID 580898611-(2-Bromo-6-fluoro-phenyl)-propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of EtMgBr (35 mL, 35 mmol) in THF (1 M) is added dropwise to a solution of 2-bromo-6-fluoro-benzaldehyde (7 g, 34.5 mmol) in THF at −78° C. The mixture is stirred for 1 hour at −78° C. Saturated NH4Cl is added dropwise to the mixture which is subsequently warmed to room temperature and stirred for 1 hour. The organic layer is separated, extracted with THF (3×100 mL). The combined organic layers are washed with brine, dried and solvent is removed in vacuo. The crude product is purified by flash chromatography (5% EtOAc/hexanes) to obtain 1-(2-bromo-6-fluoro-phenyl)-propan-1-ol.

Workup

  1. temperatureis subsequently warmed to room temperature
  2. stirringstirred for 1 hour
  3. customThe organic layer is separated
  4. extractionextracted with THF (3×100 mL)
  5. washThe combined organic layers are washed with brine
  6. customdried
  7. customsolvent is removed in vacuo
  8. customThe crude product is purified by flash chromatography (5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7fad2649a99e4494ac93a76eb3a16e24
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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