4-Bromophthalic anhydride → (5-Bromo-2-(hydroxymethyl)phenyl)methanol

HRID 1057150노트

반응식

HRID 1057150 반응식
[Li].[Br:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][C:6]2=O>C1COCC1>[Br:2][C:3]1[CH:11]=[CH:10][C:9]([CH2:8][OH:12])=[C:5]([CH2:6][OH:7])[CH:4]=1

참가 물질

4

반응물 2

HCID 665904-Bromophthalic anhydrideHCID 3028194Lithium

생성물 1

HCID 10798791(5-Bromo-2-(hydroxymethyl)phenyl)methanol수율 125.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-30 °C

실험 절차

Lithium aluminumhydride (320 mg, 8.81 mmol) was added to a solution of 5-bromoisobenzofuran-1,3-dione (1 g, 4.4 mmol) in THF at room temperature. The mixture was heated at reflux for 3 h, cooled to −30° C., and then quenched with water. The mixture was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to afford the title compound (1.2 g). 1HNMR (400 MHz, DMSO-d6): δ 7.54 (d, 1H), 7.42 (dd, 1H), 7.33-7.31 (m, 1H), 5.23 (t, 1H), 5.15 (t, 1H), 4.51 (d, 2H), 4.45 (d, 2H).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. customquenched with water
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-10dcd6056040454c9749672c278b3bc2
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399646B2

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