Methyl chloroacetate → 6-Bromo-1-benzofuran-2-carboxylic acid

HRID 1012688

반응식

HRID 1012688 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([OH:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C:19]([O:21]C)=[O:20].[OH-].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]2[CH:6]=[C:18]([C:19]([OH:21])=[O:20])[O:10][C:4]=2[CH:3]=1

참가 물질

8

반응물 4

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 40660194-Bromo-2-hydroxybenzaldehyde

생성물 1

HCID 14744716-Bromo-1-benzofuran-2-carboxylic acid

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
130 °C

실험 절차

8.0 g (39.8 mmol) of 4-bromo-2-hydroxybenzaldehyde and 1.47 g (3.98 mmol) of tetra-n-butylammonium iodide are mixed with 22 g (159.19 mmol) of anhydrous potassium carbonate. 9.07 g (83.57 mmol) of methyl chloroacetate are added. The reaction mixture is heated at 130° C. for 4 h and then cooled to 0° C. in an ice bath. 100 ml of THF and a solution of 13.4 g (238.8 mmol) of potassium hydroxide in 50 ml of water are added, and the mixture is then stirred at RT overnight. The THF is removed under reduced pressure. The remaining aqueous phase is diluted with water and acidified with conc. hydrochloric acid. The precipitated product is filtered off and dried under high vacuum. Silica gel 60 (Merck, Darmstadt; eluent: toluene, toluene/acetic acid 50:1, toluene/acetic acid/methyl acetate 35:1:5) is used for final purification. The solvent is removed under reduced pressure. Finally, the last residues of solvent are removed under high vacuum. 3.8 g (40% of theory) of the title compound are isolated.

후처리

  1. temperaturecooled to 0° C. in an ice bath
  2. customThe THF is removed under reduced pressure
  3. additionThe remaining aqueous phase is diluted with water
  4. filtrationThe precipitated product is filtered off
  5. customdried under high vacuum
  6. custompurification
  7. customThe solvent is removed under reduced pressure
  8. customFinally, the last residues of solvent are removed under high vacuum

출처 및 근거

ORD 기록
ord-1f0c50e081ca498b8bc14b3261f436ef
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977485B2

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