4-Chloro-3-Fluorobenzaldehyde → 1-(4-Chloro-3-fluorophenyl)ethan-1-ol

HRID 1744876Notes

Reaction equation

HRID 1744876 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[F:10].[CH3:11]COCC.C[Mg+].[Br-]>C1COCC1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH3:11])=[CH:4][C:3]=1[F:10]

Participants

4

Reactant 2

HCID 27249854-Chloro-3-FluorobenzaldehydeHCID 178467672HCID 178467672, compound

Product 1

HCID 219347441-(4-Chloro-3-fluorophenyl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

To a solution of 4-chloro-3-fluorobenzaldehyde (1 eq) in THF (0.3 M) at −78° C. was added 3M/Et2O MeMgBr (1.5 eq). The reaction mixture was stirred at −50° C. for 3 hrs, quenched with aqueous saturated NH4Cl and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated to give 1-(4-chloro-3-fluorophenyl)ethanol, which was used as such for the next step.

Workup

  1. customquenched with aqueous saturated NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fe10e2668635412bb68af3e8a73e6205
Source dataset
uspto-grants-2006_03
Patent number
US07019022B2

Reaction notes

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