Sodium Acetate → 2-Bromo-4-(4-ethoxybenzoyl)benzyl acetate

HRID 1716948ノート

反応式

HRID 1716948 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH3:20])=[CH:14][CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH2:8]Br.[C:21]([O-:24])(=[O:23])[CH3:22].[Na+]>CN(C=O)C.O>[C:21]([O:24][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([C:10](=[O:11])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH3:20])=[CH:14][CH:13]=2)=[CH:3][C:2]=1[Br:1])(=[O:23])[CH3:22]

参加物

5

反応物 2

HCID 517045Sodium AcetateHCID 59013439(3-Bromo-4-(bromomethyl)phenyl)(4-ethoxyphenyl)methanone

生成物 1

HCID 590134512-Bromo-4-(4-ethoxybenzoyl)benzyl acetate収率 95%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
68 °C

実験手順

To a solution of (3-bromo-4-(bromomethyl)phenyl)(4-ethoxyphenyl)methanone (0.456 g, 1.15 mmol) in 15 mL of DMF was added sodium acetate (0.188 g, 2.29 mmol). After being stirred for 2.5 h at 68° C., the mixture was diluted with 15 mL of H2O and extracted 3× with ethyl acetate. The combined organic layers were washed once with saturated NH4Cl, once with saturated brine and dried over Na2SO4. Concentration under reduced pressure gave 0.412 g of the crude product, which was used in the next step without further purification. 1H NMR (CDCl3, 300 MHz): δ 7.95 (d, J=1.2 Hz, 1H), 7.79 (d, J=8.8 Hz, 2H), 7.68 (dd, J=1.2, 8.0 Hz, 1H), 7.50 (d, J=8.0 Hz, 1H), 6.95 (d, J=8.8 Hz, 2H), 5.25 (s, 2H), 4.12 (q, J=7.0 Hz, 2H), 1.46 (t, J=7.0 Hz, 3H); MS ESI (m/z) 377 (M+1)+, calc. 376.

後処理

  1. extractionextracted 3× with ethyl acetate
  2. washThe combined organic layers were washed once with saturated NH4Cl, once with saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationConcentration under reduced pressure

出典と根拠

ORDレコード
ord-917a75c88fb848a990c8b8a7c023b8ec
出典データセット
uspto-grants-2010_09
特許番号
US07803778B2

反応ノート

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