1-Bromonaphthalene-2-carbaldehyde → (1-Bromonaphthalen-2-yl)methanol

HRID 1596046

Reaction equation

HRID 1596046 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:12]=[O:13].[BH4-].[Na+]>CO>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][OH:13]

Participants

4

Reactant 2

HCID 769091-Bromonaphthalene-2-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 13113200(1-Bromonaphthalen-2-yl)methanolYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-bromo-2-naphthaldehyde (2.12 g, 8.91 mmol) in MeOH under N2 at 0° C. was treated with NaBH4 (0.51 g, 13.4 mmol), stirred for 15 minutes, quenched with acetone, and concentrated. Purification on silica gel with 5% ethyl acetate/CH2Cl2 provided 1.95 g (92%) of the desired compound as a white solid.

Workup

  1. customquenched with acetone
  2. concentrationconcentrated
  3. customPurification on silica gel with 5% ethyl acetate/CH2Cl2

Sources & evidence

ORD record
ord-6e3aac090eda42cfb50f990f50991962
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Linked notes

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