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

HRID 2248020Notes

Reaction equation

HRID 2248020 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 73%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1049PyridineSolvent

Procedure

A heterogeneous mixture of 3-hydroxybenzaldehyde (9.16 g, 75 mmol), 4-bromofluorobenzene (27.30 g, 156 mmol), K2CO3 (16.07 g, 116.3 mmol) and copper powder (2.38 g, 37.5 mmol) in pyridine (75 mL) was refluxed for 40 hrs. It was then cooled to room temperature and filtered through Celite. The filtrate was diluted with ethylacetate (500 mL) and washed with water (3×300 mL). The organic was then dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, hexane:ether, 85:15) to afford 11.83 g (73%) of 3-(4-fluorophenoxy)benzaldehyde as a yellow oil.

Workup

  1. temperaturewas refluxed for 40 hrs
  2. filtrationfiltered through Celite
  3. additionThe filtrate was diluted with ethylacetate (500 mL)
  4. washwashed with water (3×300 mL)
  5. dry with materialThe organic was then dried with MgSO4
  6. concentrationconcentrated
  7. customThe resulting residue was chromatographed (silica gel, hexane:ether, 85:15)

Sources & evidence

ORD record
ord-1209d6fdb25640d4a2c9075b97a2d6fc
Source dataset
uspto-grants-1991_08
Patent number
US05037853

Reaction notes

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