Benzaldehyde → 4-Fluorobenzhydrol

HRID 2202604Notes

Reaction equation

HRID 2202604 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([Mg]Br)=[CH:12][CH:11]=1.Cl>O1CCCC1>[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[OH:8])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 178418676HCID 178418676, compound

Product 1

HCID 5707534-FluorobenzhydrolYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Benzaldehyde (8.5 g, 80 mmol) was dissolved in 100 mL of tetrahydrofuran and cooled in an ice bath. Then, a 1.0-M solution (88 mL, 88 mmol) of 4-fluorophenylmagnesium bromide in tetrahydrofuran was added dropwise thereto at 0° C. After the dropping was completed, the mixture was heated to a room temperature, and the completion of the reaction was confirmed by TLC. After the completion of the reaction, the reaction mixture was poured into 5% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and dried over sodium sulfate, and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (chloroform/ethanol (volume ratio)=10:1) to give the title compound (13 g, 81%).

Workup

  1. temperaturecooled in an ice bath
  2. customat 0° C
  3. customAfter the completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationthe solvent was distilled off
  8. customThe resulting residue was purified by silica gel column chromatography (chloroform/ethanol (volume ratio)=10:1)

Sources & evidence

ORD record
ord-7256f143fb2c4fd5b1af80825220c307
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

Loading…