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Hydrochloric Acid → Methyl 4-bromo-5-cyano-3-methylthiophene-2-carboxylate

HRID 1723925
ノート
印刷プレビュー

反応式

HRID 1723925 の反応式
Cl.[NH2:2]O.[Br:4][C:5]1[C:6]([CH3:16])=[C:7]([C:12]([O:14][CH3:15])=[O:13])[S:8][C:9]=1[CH:10]=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.Cl>C(#N)C.N1C=CC=CC=1.C(OCC)(=O)C>[Br:4][C:5]1[C:6]([CH3:16])=[C:7]([C:12]([O:14][CH3:15])=[O:13])[S:8][C:9]=1[C:10]#[N:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 9845Trifluoroacetic anhydrideHCID 443297Hydroxyamine hydrochlorideHCID 71378553Methyl 4-bromo-5-formyl-3-methylthiophene-2-carboxylate

生成物 1

HCID 66570703Methyl 4-bromo-5-cyano-3-methylthiophene-2-carboxylate収率 91.5%

試薬・触媒・溶媒 3

HCID 1049
Pyridine
溶媒
HCID 6342Acetonitrile溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

Hydroxylamine hydrochloride (5 g, 72 mmol) was added to a solution of methyl 4-bromo-5-formyl-3-methylthiophene-2-carboxylate (16.5 g, 63 mmol) in acetonitrile (175 mL) and pyridine (30 mL). The resulting solution was stirred at room temperature for 2 h, then trifluoroacetic anhydride (21.3 mL, 153 mmol). After 3 h the reaction mixture was poured into ethyl acetate and aqueous hydrochloric acid. The organic layer was separated, washed with hydrochloric acid and water, dried over sodium sulphate and evaporated. The resulting raw material was triturated with 90 mL of a water/ethyl alcohol mixture (1:1) and dried under vacuum to give 15 g of the title compound, used in the following step without further purification.

後処理

  1. customThe organic layer was separated
  2. washwashed with hydrochloric acid and water
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customThe resulting raw material was triturated with 90 mL of a water/ethyl alcohol mixture (1:1)
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-bf84f696bcbc4a7fa3c39ce7c7c169b3
出典データセット
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07485661B2

反応ノート

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