Hydrochloric Acid → (5-Bromo-2,3-dihydro-1-benzofuran-7-yl)methanol

HRID 2247417Notes

Reaction equation

HRID 2247417 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([CH:11]=[O:12])[C:5]2[O:6][CH2:7][CH2:8][C:4]=2[CH:3]=1.[BH4-].[Na+].Cl>O1CCCC1.C(O)C>[Br:1][C:2]1[CH:10]=[C:9]([CH2:11][OH:12])[C:5]2[O:6][CH2:7][CH2:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 27948045-Bromo-2,3-dihydrobenzo[b]furan-7-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 22930441(5-Bromo-2,3-dihydro-1-benzofuran-7-yl)methanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-2,3-dihydrobenzo[b]furan-7-carbaldehyde (11.42 g), was dissolved in 50 ml of tetrahydrofuran and 50 ml of ethanol, then 2 g of sodium borohydride was added thereto, and the mixture was stirred overnight at room temperature. 1 N hydrochloric acid was added to the reaction mixture which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed, to give (5-bromo-2,3-dihydrobenzo[b]furan-7-yl)methanol. This product was treated in the same way as Production Example 90b) to give 12.6 g of the title compound.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-d8798db2100248e0a52bf159032a548a
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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