Fluorobenzene → HCID 22175464, compound

HRID 1797503Notes

Reaction equation

HRID 1797503 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1.[Cl-].[Al+3].[Cl-].[Cl-].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:9]([C:4]2[CH:3]=[C:2]([Br:1])[CH:12]=[CH:11][C:5]=2[C:6]([OH:8])=[O:7])=[O:10])=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 10008FluorobenzeneHCID 665904-Bromophthalic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22175464HCID 22175464, compoundYield 10%

Procedure

To a solution of 4-bromophthalic anhydride (50 g, 220 mmol) in fluorobenzene (300 mL) was added aluminum chloride (60 g, 450 mmol) by small portions under ice-cooling. The-obtained mixture was stirred at room temperature for 15 h. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-diisopropyl ether and the precipitated crystals were collected by filtration. The crystals were recrystallized from ethyl acetate to give a solid of a mixture (9:1)(7 g, 10%) of 2-(4-fluorobenzoyl)-4-bromobenzoic acid and 2-(4-fluorobenzoyl)-5-bromobenzoic acid. (2-(4-fluorobenzoyl)-4-bromobenzoic acid: 1H-NMR(CDCl3) δ: 7.06–7.17 (2H, m), 7.50 (1H, d, J=2.0 Hz), 7.69–7.79 (3H, m), 7.95 (1H, d, J=8.4 Hz).

Workup

  1. temperaturecooling
  2. customThe-obtained mixture
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with 1N hydrochloric acid and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from ethyl acetate-diisopropyl ether
  8. filtrationthe precipitated crystals were collected by filtration
  9. customThe crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-58e7d5bbd32049c3961d600098c0333c
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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