N-bromobutanimide → Methyl 2-(3-bromo-5-formyl-4-hydroxyphenyl)acetate

HRID 712932

반응식

HRID 712932 반응식
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH:12]=[O:13])[CH:6]=1.[Br:15]N1C(=O)CCC1=O>CN(C=O)C.C(OC(=O)C)(C)C.C(O)(C)C>[Br:15][C:9]1[CH:10]=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:14])[CH:6]=[C:7]([CH:12]=[O:13])[C:8]=1[OH:11]

참가 물질

6

반응물 2

HCID 67184N-bromobutanimideHCID 12374099Methyl 2-(3-formyl-4-hydroxyphenyl)acetate

생성물 1

HCID 57198039Methyl 2-(3-bromo-5-formyl-4-hydroxyphenyl)acetate수율 84.8%

시약·촉매·용매 3

HCID 3776Isopropanol용매HCID 6228Dimethylformamide용매2회HCID 7915Isopropyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a 2 L round bottom flask with magnetic stirrer, thermocouple, and ice water bath was added (3-formyl-4-hydroxyphenyl)acetic acid methyl ester (308 g, 1.59 mol) and N,N-dimethylformamide (1 L). The reaction mixture was stirred and cooled to −5 to 5° C. A solution of N-bromosuccinimide (311 g, 1.75 mol) in DMF (1.5 to 2 L) was added dropwise, at such a rate to keep the internal temperature between 5 and 10° C. Once the addition was complete, the reaction mixture was allowed to warm to room temperature and monitored for completion by HPLC analysis. The reaction time was about 4 h. The reaction mixture was diluted with isopropylacetate (3 L), and the resulting solution was extracted with water to remove the DMF. Concentration of the organic phase afforded a reddish solid that was dissolved in hot isopropanol (400 mL) and allowed to cool while stirring. The resulting off-white crystalline product was filtered and washed with cold IPA (−20° C.; 400 mL) to yield methyl (3-bromo-5-formyl-4-hydroxyphenyl)acetate (368 g, 84.7%) as off-white crystals.

후처리

  1. customthe internal temperature between 5 and 10° C
  2. additionOnce the addition
  3. temperatureto warm to room temperature
  4. extractionthe resulting solution was extracted with water
  5. customto remove the DMF
  6. customConcentration of the organic phase afforded a reddish solid
  7. temperatureto cool
  8. stirringwhile stirring
  9. filtrationThe resulting off-white crystalline product was filtered
  10. washwashed with cold IPA (−20° C.; 400 mL)

출처 및 근거

ORD 기록
ord-d1aa33862eb8490bbb282705ded56d0a
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181280B2

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