3-Bromo-4-hydroxyphenylacetic acid → HCID 18669494, 화합물

HRID 1058980

반응식

HRID 1058980 반응식
[OH:1][C:2]1([CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([OH:11])[CH2:5]1)C=O.[Br:12][C:13]1[CH:14]=[C:15]([CH2:20][C:21](O)=[O:22])[CH:16]=[CH:17][C:18]=1[OH:19]>O=P(Cl)(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[OH:10][C:8]1[CH:7]=[C:6]([OH:11])[CH:5]=[C:2]([OH:1])[C:9]=1[C:21](=[O:22])[CH2:20][C:15]1[CH:16]=[CH:17][C:18]([OH:19])=[C:13]([Br:12])[CH:14]=1

참가 물질

5

반응물 2

HCID 27696283-Bromo-4-hydroxyphenylacetic acidHCID 86758840HCID 86758840, 화합물

생성물 1

HCID 18669494HCID 18669494, 화합물수율 18.4%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 24813Phosphorus oxychloride용매

실험 절차

1,3.5-Trihydroxybenzaldehyde (1.01 g, 6.95 mmol) and 3-bromo-4-hydroxyphenylacetic acid (1.44 g, 6.25 mmol) were suspended in POCl3 (4 mL). After 1 min, an exothermic reaction occurred. The mixture was allowed to cool to room temperature. Zinc chloride (1M ether solution, 4.7 mmol) was added and the mixture was heated at 75° C. for 1 h. After cooling, the mixture was partitioned in ethyl acetate and 1 M aqueous HCl. The organic layer was washed with brine and dried with MgSO4. Purification on silica gel (MeOH/dichloromethane, gradient) afforded 1-(2,4,6-trihydroxyphenyl)-2-(3-bromo-4-hydroxyphenyl)ethanone (390 mg) as a tan solid.

후처리

  1. customan exothermic reaction
  2. temperaturethe mixture was heated at 75° C. for 1 h
  3. temperatureAfter cooling
  4. customthe mixture was partitioned in ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried with MgSO4
  7. customPurification on silica gel (MeOH/dichloromethane, gradient)

출처 및 근거

ORD 기록
ord-44e7a381190c4664b0aa1416fad2b5cb
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06518301B1

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