Cesium carbonate → Tert-butyl 2-(2-bromo-4-formylphenoxy)acetate

HRID 68583

反応式

HRID 68583 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[O:6])[CH:7]=[CH:8][C:9]=1[O:10][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 763083-Bromo-4-hydroxybenzaldehydeHCID 79177tert-Butyl bromoacetate

生成物 1

HCID 17999215Tert-butyl 2-(2-bromo-4-formylphenoxy)acetate収率 98.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-bromo-4-hydroxybenzaldehyde (5 g, 25 mmol, 1 eq, Aldrich, Milwaukee, Wis., USA) in DMF (200 mL) was added solid cesium carbonate (16.25 g, 50 mmol, 2 eq) followed by dropwise addition of t-butyl 2-bromoacetate (4.4 mL, 30 mmol, 1.2 eq, Aldrich, Milwaukee, Wis., USA). After stirring at room temperature for 18 h, the DMF was removed in vacuo and the resultant residue was extracted between EtOAc (50 mL) and brine (50 mL). The separated organic layer was dried (Na2SO4), and concentrated in vacuo to give 7.74 g (98.4%) of t-butyl 2-(2-bromo-4-formylphenoxy)acetate (1). 1HNMR (CDCl3, 300 MHz): δ 9.83 (s, 1H), 8.08 (d, 1H), 7.76 (dd, 1H), 6.83 (d, 1H), 4.67 (s, 1H).1.44 (s, 9H).

後処理

  1. customthe DMF was removed in vacuo
  2. extractionthe resultant residue was extracted between EtOAc (50 mL) and brine (50 mL)
  3. dry with materialThe separated organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-03cdefa305c4419ab250d0cc1ffdea8f
出典データセット
uspto-grants-2014_09
特許番号
US08822467B2

関連ノート

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