5-Bromo-2-chlorobenzaldehyde → (4-benzylspiro[3H-1,4-benzoxazine-2,1-cyclopropane]-6-yl)-(5-bromo-2-chloro-phenyl)methanol

HRID 72593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 72593
[CH2:1]([N:8]1[C:15]2[CH:16]=[C:17](Br)[CH:18]=[CH:19][C:14]=2[O:13][C:10]2([CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[Br:26][C:27]1[CH:28]=[CH:29][C:30]([Cl:35])=[C:31]([CH:34]=1)[CH:32]=[O:33]>C1COCC1>[CH2:1]([N:8]1[C:15]2[CH:16]=[C:17]([CH:32]([C:31]3[CH:34]=[C:27]([Br:26])[CH:28]=[CH:29][C:30]=3[Cl:35])[OH:33])[CH:18]=[CH:19][C:14]=2[O:13][C:10]2([CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 106089255-Bromo-2-chlorobenzaldehydeHCID 583407784-benzyl-6-bromo-spiro[3H-1,4-benzoxazine-2,1-cyclopropane]HCID 178418339Butyllithium

Produkt 1

HCID 58340780(4-benzylspiro[3H-1,4-benzoxazine-2,1-cyclopropane]-6-yl)-(5-bromo-2-chloro-phenyl)methanolAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 4-benzyl-6-bromo-spiro[3H-1,4-benzoxazine-2,1′-cyclopropane] (1.12 g, 3.4 mmol) in THF (10 mL) was added 1.6 M solution of n-BuLi in hexanes (2.12 mL, 3.4 mmol) at −78° C. The reaction mixture was stirred for 30 min, and then transferred to a stirred solution of 5-bromo-2-chlorobenzaldehyde (745 mg, 3.4 mmol) in THF (10 mL) at −78° C. After stirring for 1 h, the reaction was quenched by the addition of saturated ammonium chloride solution and extracted with ethyl acetate. The ethyl acetate layer was washed with water, brine, dried over sodium sulphate, and concentrated. The resulting residue was purified by silica gel column chromatography to furnish (4-benzylspiro[3H-1,4-benzoxazine-2,1′-cyclopropane]-6-yl)-(5-bromo-2-chloro-phenyl)methanol (790 mg).

Aufarbeitung

  1. stirringAfter stirring for 1 h
  2. customthe reaction was quenched by the addition of saturated ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water, brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1095a317c9f94cce927d82697dbedff0
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828951B2

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