Ethanol → 4-Bromo-2-(diethoxymethyl)thiophene

HRID 40948노트

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HRID 40948 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1.[CH2:9]([OH:11])[CH3:10].[Cl-].[NH4+].C([O-])([O-])O[CH2:16][CH3:17]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]([O:11][CH2:9][CH3:10])[O:8][CH2:16][CH3:17])[S:5][CH:6]=1

참가 물질

5

반응물 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 877924-Bromothiophene-2-carbaldehydeHCID 53630039Ethylorthoformate

생성물 1

HCID 122800244-Bromo-2-(diethoxymethyl)thiophene수율 81%

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온도
60 °C

실험 절차

A mixture of 4-bromothiophene-2-carbaldehyde (1.2 g, 0.0063 mol) in ethanol (10 mL, 0.2 mol) was treated with ammonium chloride (0.42 g, 0.0078 mol) and ethyl orthoformate (1.2 g, 0.0078 mol). The mixture was stirred at 60° C. for 2 hours. The reaction was quenched with water and extracted with ethyl acetate. The combined organic layer was washed with saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to give 4-bromo-2-(diethoxymethyl)thiophene as an oil (1.3 g, 81%). 1H NMR (400 MHz, CDCl3): δ□ 7.22 (s, 1H), 6.99 (s, 1H), 5.68 (s, 1H), 3.63 (q, 4H) 1.24 (t, 6H).

후처리

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9c7dc7f272d74b8fa26ea2c736107aea
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530485B2

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