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

HRID 68583

반응식

HRID 68583 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-03cdefa305c4419ab250d0cc1ffdea8f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822467B2

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