Sodium borohydride → (4-Bromo-7-methoxybenzofuran-2-yl)-methanol

HRID 1108317Notes

Reaction equation

HRID 1108317 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[O:6][C:7]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([Br:16])[C:8]=2[CH:9]=1)=[O:4]>C(O)CCC>[Br:16][C:10]1[C:8]2[CH:9]=[C:5]([CH2:3][OH:4])[O:6][C:7]=2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 187848644-Bromo-7-methoxy-1-benzofuran-2-carbaldehyde

Product 1

HCID 18784868(4-Bromo-7-methoxybenzofuran-2-yl)-methanolYield 86%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Sodium borohydride (1.12 g) was added portionwise to a stirred solution of 2-formyl-4-bromo-7-methoxybenzofuran (30 g) in 1-butanol (150 ml) at ambient temperature. After stirring for 1 h the reaction was quenched by the addition of 2M hydrochloric acid (100 ml) and stirred overnight. The mixture was separated and the organic phase washed with water (200 ml). The combined aqueous phases were extracted with tert-butyl methyl ether (100 ml). The organic phases were combined and concentrated in vacuo followed by drying in vacuo at 60° C. to afford the title compound as a brown solid (26 g).

Workup

  1. customwas quenched by the addition of 2M hydrochloric acid (100 ml)
  2. stirringstirred overnight
  3. customThe mixture was separated
  4. washthe organic phase washed with water (200 ml)
  5. extractionThe combined aqueous phases were extracted with tert-butyl methyl ether (100 ml)
  6. concentrationconcentrated in vacuo
  7. customby drying in vacuo at 60° C.

Sources & evidence

ORD record
ord-d7b26369c3a54cf6bc0c68d78ec08041
Source dataset
uspto-grants-2000_05
Patent number
US06066657

Reaction notes

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