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

HRID 1057150ノート

反応式

HRID 1057150 の反応式
[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

参加物

4

反応物 2

HCID 665904-Bromophthalic anhydrideHCID 3028194Lithium

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-30 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-10dcd6056040454c9749672c278b3bc2
出典データセット
uspto-grants-2016_07
特許番号
US09399646B2

反応ノート

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