Water → 3-Benzoyloxy-4-fluorobenzyl bromide

HRID 901170

Reaktionsgleichung

Reaktionsgleichung von HRID 901170
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl.C(OCC)C>[Br:18][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:9][C:10](=[O:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:4]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 167492203-Benzoyloxy-4-fluorotoluene

Produkt 1

HCID 167478383-Benzoyloxy-4-fluorobenzyl bromide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of benzoic acid 2-fluoro-5-methyl-phenyl ester (CAB02145, 2.47 g, 10.0 mmol), N-bromo-succinimide (1.96 g, 11.0 mmol) and dibenzoy lperoxide (10 mg) in carbon tetrachloride (25 mL) was heated to reflux for 2 h (TLC monitored). After cooling to room temperature, water (50 mL) and diethyl ether (100 mL) were added. The organic layer was separated, washed with brine (20 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography (EtOAc:hexane, 1:25, Rf: 0.28). Yield: 1.80 g (58%), white solid. 1H-NMR (400 MHz, CDCl3) δ=4.48 (s, 2H, —CH2Br), 7.18 (dd, J=9.8, 8.6 Hz, 1H), 7.28 (ddd, J=8.6, 4.3, 2.3 Hz, 1H), 7.34 (dd, J=7.0, 2.3 Hz, 1H), 7.50-7.55 (m, 2H), 7.64-7.69 (m, 1H), 8.18-8.23 (m, 2H). LRMS (FAB+): 229.1 (95), 309.0 (100, [M+H]+). Found: C, 54.1; H, 3.22%; C14H10BrFO2 (309.13) requires C, 54.39; H, 3.26%.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 2 h (TLC monitored)
  3. customThe organic layer was separated
  4. washwashed with brine (20 mL)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (EtOAc:hexane, 1:25, Rf: 0.28)

Quellen und Nachweise

ORD-Eintrag
ord-2c4bbc835baa4e0a90fec171ae26e02b
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361677B2

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