Water → Methyl 4-bromo-3-methoxythiophene-2-carboxylate

HRID 479284

反応式

HRID 479284 の反応式
[Br:1][C:2]1[C:3]([OH:11])=[C:4]([C:7]([O:9][CH3:10])=[O:8])[S:5][CH:6]=1.CI.[C:14]([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[Br:1][C:2]1[C:3]([O:11][CH3:14])=[C:4]([C:7]([O:9][CH3:10])=[O:8])[S:5][CH:6]=1

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2777611Methyl 4-bromo-3-hydroxythiophene-2-carboxylate

生成物 1

HCID 2736824Methyl 4-bromo-3-methoxythiophene-2-carboxylate収率 95.6%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of 36 g (0.15 mole) of methyl 4-bromo-3-hydroxy-2-thiophenecarboxylate in 300 mL of dimethyl sulfoxide (DMSO) was added 32 g (0.23 mole) of methyl iodide and then 32 g of powdered K2CO3. After 2 hr, the reaction mixture was poured into water and extracted with ether. The organic phase was washed with water (4×200 mL), dried over MgSO4, filtered and concentrated to give 36 g of a colorless solid. 1H NMR (300 MHz, CDCl3): δ 7.4 (s, 1H); 4.0 (s, 3H); 3.9 (s, 3H). Anal. Calc'd for C7H7BrO3S: C, 33.48; H, 2.81; S, 12.77. Found: C, 33.18; H, 2.70; S, 12.49.

後処理

  1. extractionextracted with ether
  2. washThe organic phase was washed with water (4×200 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-8cbb7dfa86b3486483d3ea847e70e751
出典データセット
uspto-grants-2003_11
特許番号
US06645918B1

関連ノート

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