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

HRID 1723925
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반응식

HRID 1723925 반응식
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]
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참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 1049
Pyridine
용매
HCID 6342Acetonitrile용매
HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bf84f696bcbc4a7fa3c39ce7c7c169b3
출처 데이터셋
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07485661B2

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