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

HRID 1241478Notes

Reaction equation

HRID 1241478 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][Li]>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 178418348HCID 178418348, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-3-fluoro-benzaldehyde (5.14 g, 32.4 mmol) was dissolved in THF (100 mL) and place at −78° C. under nitrogen atmosphere. Methyl Lithium (1.6 M in diethyl ether, 22.3 mL) was added to the reaction during a period of 3 minutes maintianing the same temperature. After the addition, the reaction was stirred at room temperature for 1 h. Then, the reaction was poured over ice water and extracted with ethyl acetate and hydrochloric acid 1N. The organic layer was collected, dried with sodium sulfate, filtered and concentrated under vacuum to produce a crude, which it was chromatograph over silica gel using 50% hexane-ethyl Acetate as solvent to yield 5.1 g of 1-(4-chloro-3-fluoro-phenyl)-ethanol. 1H NMR (400 MHz, Cl3CD) δ 7.37 (t, J=8.14 Hz, 1H), 7.20 (dd, J=1.86, 10.00 Hz, 1H), 7.09 (dd, J=1.86, 8.14 Hz, 1H), 4.89 (m, 1H), 1.93 (br s, 1H), 1.49 (d, J=6.51, 3H).

Workup

  1. customat −78° C.
  2. additionAfter the addition
  3. extractionextracted with ethyl acetate and hydrochloric acid 1N
  4. customThe organic layer was collected
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customto produce a crude, which it

Sources & evidence

ORD record
ord-a41fc73086974eb095e87469a8d4e5f7
Source dataset
uspto-grants-2006_10
Patent number
US07115598B2

Reaction notes

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