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

HRID 1817595Notes

Reaction equation

HRID 1817595 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

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

Conditions

Temperature
60 °C

Procedure

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)thio-phene 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).

Workup

  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

Sources & evidence

ORD record
ord-9a893d45c4cd4192bed63dd71ad4ce80
Source dataset
uspto-grants-2009_10
Patent number
US07598257B2

Reaction notes

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