Bromine → Ethyl 8-bromo-2,2-dimethylchroman-6-carboxylate

HRID 1417708

Reaktionsgleichung

Reaktionsgleichung von HRID 1417708
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=2)[O:3]1.[Br:18]Br>CC(O)=O>[Br:18][C:5]1[CH:6]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[C:9]2[C:4]=1[O:3][C:2]([CH3:17])([CH3:1])[CH2:11][CH2:10]2

Komponenten

4

Edukt 2

HCID 24408BromineHCID 246672Ethyl 2,2-dimethylchroman-6-carboxylate2×

Produkt 1

HCID 10519233Ethyl 8-bromo-2,2-dimethylchroman-6-carboxylateAusbeute 110,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2,2-dimethylchroman-6-carboxylate (Compound 216, 500 mg, 2.14 mmol) in HOAc (4 mL) was added Br2 (0.11 mL, 2.14 mmol). The reaction mixture was stirred at room temperature overnight and then a stream of air was passed through the reaction mixture to remove the excess Br2. Removal of the solvent under reduced pressure and column chromatography using the residue (EtOAc:hexanes1:9) afforded 741 mg (100%) of the title compound as an oil. 1H NMR δ 8.05 (1H, d, J=2.2 Hz), 7.73 (1H, d, J=2.2 Hz), 4.34 (2H, q, J=7.1 Hz), 2.84 (2H, t, J=6.7 Hz), 1.85 (2H, t, J=6.7 Hz), 1.40 (6H, s), 1.38 (3H, t, J=7.2 Hz). Anal (C14H17BrO3.0.2 H2O) C, H.

Aufarbeitung

  1. customto remove the excess Br2
  2. customRemoval of the solvent under reduced pressure and column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-86a21189e8e74b7888003b54e41c64e4
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05877207

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