2-Bromo-2-methylpropionyl bromide → Methyl {4-[4-(2-bromo-2-methylpropanoyl)phenyl]bicyclo[2.2.2]oct-1-yl}acetate

HRID 908114Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908114
[C:1]1([C:7]23[CH2:14][CH2:13][C:10]([CH2:15][C:16]([O:18][CH3:19])=[O:17])([CH2:11][CH2:12]2)[CH2:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Br:24][C:25]([CH3:30])([CH3:29])[C:26](Br)=[O:27]>C(Cl)Cl>[Br:24][C:25]([CH3:30])([CH3:29])[C:26]([C:4]1[CH:3]=[CH:2][C:1]([C:7]23[CH2:8][CH2:9][C:10]([CH2:15][C:16]([O:18][CH3:19])=[O:17])([CH2:13][CH2:14]2)[CH2:11][CH2:12]3)=[CH:6][CH:5]=1)=[O:27]

Komponenten

5

Edukt 3

HCID 886852-Bromo-2-methylpropionyl bromideHCID 6451240Aluminum(III) ChlorideHCID 25016427Methyl (4-phenylbicyclo[2.2.2]oct-1-yl)acetate2×

Produkt 1

HCID 25258107Methyl {4-[4-(2-bromo-2-methylpropanoyl)phenyl]bicyclo[2.2.2]oct-1-yl}acetateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To an ice water cooled solution of methyl (4-phenylbicyclo[2.2.2]oct-1-yl)acetate (Intermediate 8; 3.88 g, 15.02 mmol) in DCM (150 mL) was added aluminium chloride (6.01 g, 45.05 mmol) followed by the dropwise addition of 2-bromoisobutyryl bromide (1.86 mL, 15.02 mmol). The reaction mixture was allowed to stir at ˜0° C. for 30 mins then poured onto ice-water (20 mL). The organic phase was separated and the aqueous phase washed with DCM (2×150 mL), the organic washings combined, dried (MgSO4) and concentrated to leave a yellow gum. This was purified on a 120 g Crawford silica cartridge, loading in DCM and eluting with 0-10%-20% isohexane-EtOAc to give the product as a white solid (5.18 g, 12.72 mmol, 85%). 1H NMR (CDCl3) δ 1.64-1.69 (6H, m), 1.83-1.88 (6H, m), 2.03 (6H, s), 2.18 (2H, s), 3.66 (3H, s), 7.36 (2H, d), 8.10 (2H, d); Solid Probe MS m/e M+ 407.

Aufarbeitung

  1. additionthen poured onto ice-water (20 mL)
  2. customThe organic phase was separated
  3. washthe aqueous phase washed with DCM (2×150 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto leave a yellow gum
  7. customThis was purified on a 120 g Crawford silica cartridge, loading in DCM
  8. washeluting with 0-10%-20% isohexane-EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-b2b71e77414d4d82a29dcb1ab7493e5b
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017603B2

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