Boron tribromide → 6-Hydroxyisochroman-1-one

HRID 69487Notes

Reaction equation

HRID 69487 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[O:12][CH:11]=[CH:10]2>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[O:12][CH2:11][CH2:10]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 151110126-Methoxyisochromen-1-one

Product 1

HCID 552751836-Hydroxyisochroman-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1M solution of boron tribromide in methylene chloride (101 mL) was added at 0° C. to a solution of 6-methoxy-isochromen-1-one (8.9 g) in methylene chloride (178 mL). Then the ice bath was removed and the reaction mixture was stirred overnight at room temperature. Then the mixture was cooled to 0° C., water was added and the aqueous phase was extracted several times with ethyl acetate. The organic phases were combined, dried over sodium sulfate and the solvent was removed in vacuum. In this way the product was obtained with molecular weight 162.03 (C9H6O3); MS (ESI): 163 (M+H+).

Workup

  1. customThen the ice bath was removed
  2. temperatureThen the mixture was cooled to 0° C.
  3. additionwater was added
  4. extractionthe aqueous phase was extracted several times with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed in vacuum
  7. customIn this way the product was obtained with molecular weight 162.03 (C9H6O3)

Sources & evidence

ORD record
ord-66c2ac52b43d4554bf0846769ba756fa
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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