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

HRID 1057150Notes

Reaction equation

HRID 1057150 reaction equation
[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

Participants

4

Reactant 2

HCID 665904-Bromophthalic anhydrideHCID 3028194Lithium

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-10dcd6056040454c9749672c278b3bc2
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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