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

HRID 1524724Notes

Reaction equation

HRID 1524724 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)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).

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-1d8a25ff54f64b0a933e36c2adac213b
Source dataset
uspto-grants-2015_07
Patent number
US09079912B2

Reaction notes

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