3-Hydroxybenzaldehyde → Benzaldehyde, 3-(4-fluorophenoxy)-

HRID 2082086Notes

Reaction equation

HRID 2082086 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].Br[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[Cu]>[F:17][C:14]1[CH:15]=[CH:16][C:11]([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 99931-Bromo-4-fluorobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 3085320Benzaldehyde, 3-(4-fluorophenoxy)-Yield 72%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 3-hydroxybenzaldehyde (24.37 g, 199.6 mmol), 4-bromofluorobenzene (69.86 g, 399.2 mmol), potassium carbonate (42.76 g, 309.4 mnmol) and copper powder (6.34 g, 99.8 mmol) in pyridine (200 mL) was refluxed for 64 hours. It was then cooled to ambient temperature and filtered through Celite. The filtrate was diluted with ethyl acetate (600 mL) and washed with water (3×400 mL). The organic phase was dried over MgSO4. The resulting residue was chromatographed (silica gel; hexanes, ether 85:15) to afford 31.03 g (72%) of 3-(4-fluorophenoxy)benzaldehyde as a pale yellow solid.

Workup

  1. temperaturewas refluxed for 64 hours
  2. filtrationfiltered through Celite
  3. additionThe filtrate was diluted with ethyl acetate (600 mL)
  4. washwashed with water (3×400 mL)
  5. dry with materialThe organic phase was dried over MgSO4
  6. customThe resulting residue was chromatographed (silica gel; hexanes, ether 85:15)

Sources & evidence

ORD record
ord-01e14b3d4be74a7a8b7761e038757cd5
Source dataset
uspto-grants-1993_02
Patent number
US05187192

Reaction notes

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