Diisobutylaluminum hydride → 5-Bromo-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran

HRID 1453042Notes

Reaction equation

HRID 1453042 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[C:7]([CH3:12])([CH3:11])[C:6]=2[CH:13]=1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([OH:10])[C:7]([CH3:11])([CH3:12])[C:6]=2[CH:13]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 162206345-Bromo-3,3-dimethylbenzofuran-2(3H)-one

Product 1

HCID 205362245-Bromo-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-Bromo-3,3-dimethyl-3H-benzofuran-2-one (1.199 g, 5.0 mmol) (described in Step 2 of Example A(68), dissolved in anhydrous CH2Cl2 (20 ml), and cooled to −78° C., was added DIBAL (3.67 mL, 5.5 mmol, 1.5M in Toluene). The reaction was stirred for 1 h at this temperature then quenched with 1N HCl until acidic. The resulting mixture was extracted with ether, which was washed with brine, dried with MgSO4, concentrated and purified by silica gel chromatography (gradient elution 5-15% Ethylacetate/Hexanes). Yield 0.95 g, 79%.

Workup

  1. customthen quenched with 1N HCl until acidic
  2. extractionThe resulting mixture was extracted with ether, which
  3. washwas washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (gradient elution 5-15% Ethylacetate/Hexanes)

Sources & evidence

ORD record
ord-82ee8270853c4a518fe15ea930823ddc
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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