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

HRID 858594Notes

Reaction equation

HRID 858594 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-520a40089196433aaf9465e4d4b507a6
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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