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

HRID 908107ノート

反応式

HRID 908107 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To an ice water cooled solution of methyl (4-phenylbicyclo[2.2.2]oct-1-yl)acetate (536 mg, 2.07 mmol) in DCM (30 mL) was added aluminum chloride (830 mg, 6.22 mmol) followed by the dropwise addition of 2-bromoisobutyryl bromide (0.25 mL, 2.07 mmol). The reaction mixture was allowed to stir at ˜0° C. for 1 hr, then poured onto ice-water (˜20 mL). The organic phase was separated and the aqueous phase washed with DCM (3×150 mL), the organic were combined, dried (MgSO4) and concentrated to leave a yellow gum. This was purified on a 12 g silicyle silca cartridge, loading in DCM and eluting 0-10%-20% isohexane-EtOAc, to provide the title compound as a red solid, 648 mg (1.59 mmol, 77%); 1H NMR (CDCl3) δ 1.65-1.69 (m, 6H), 1.84-1.88 (m, 6H), 2.03 (s, 6H), 2.18 (s, 2H), 3.66 (s, 3H), 7.36 (d, 2H), 8.09 (d, 2H); MS m/e MH+ 377 (M−OMe).

後処理

  1. additionpoured onto ice-water (˜20 mL)
  2. customThe organic phase was separated
  3. washthe aqueous phase washed with DCM (3×150 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto leave a yellow gum
  7. customThis was purified on a 12 g silicyle silca cartridge, loading in DCM
  8. washeluting 0-10%-20% isohexane-EtOAc

出典と根拠

ORDレコード
ord-c7b591d2c6994b179bf1f1013cb19389
出典データセット
uspto-grants-2011_09
特許番号
US08017603B2

反応ノート

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