(5-Bromo-4-methoxy-3-methyl-benzofuran-2-yl)-methanol → HCID 68713008, compound

HRID 29466Notes

Reaction equation

HRID 29466 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][OH:11])=[C:7]([CH3:12])[C:6]=2[C:13]=1[O:14][CH3:15].[C:16]([Cu])#[N:17]>CN1CCCC1=O.O.C(OCC)(=O)C>[OH:11][CH2:10][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([C:16]#[N:17])=[C:13]([O:14][CH3:15])[C:6]=2[C:7]=1[CH3:12]

Participants

6

Reactant 2

HCID 68711184(5-Bromo-4-methoxy-3-methyl-benzofuran-2-yl)-methanolHCID 178418546HCID 178418546, compound

Product 1

HCID 68713008HCID 68713008, compoundYield 71.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A suspension of (5-bromo-4-methoxy-3-methyl benzofuran-2-yl)-methanol (0.31 g; 1.1 mmol, Example 136, Step 1) and CuCN (0.21 g; 2.3 mmol; 2 eq) in N-methylpyrrolidinone (1.5 mL) was subjected to microwave radiation at 200° C. for 10 minutes. The reaction was diluted with water and ethyl acetate (10 mL each) and filtered. The layers were separated and the aqueous phase was washed with a second portion of ethyl acetate. The combined organic layers were washed twice with water and once with brine. After drying over magnesium sulfate, filtration and concentration in vacuo gave the crude product. Chromatography on silica gel, eluting with 20% to 30% ethyl acetate/hexanes gave pure 2-hydroxymethyl-4-methoxy-3-methyl benzofuran-5-carbonitrile (0.17 g; 67% yield).

Workup

  1. customat 200° C.
  2. customfor 10 minutes
  3. filtrationfiltered
  4. customThe layers were separated
  5. washthe aqueous phase was washed with a second portion of ethyl acetate
  6. washThe combined organic layers were washed twice with water and once with brine
  7. dry with materialAfter drying over magnesium sulfate, filtration and concentration in vacuo
  8. customgave the crude product
  9. washChromatography on silica gel, eluting with 20% to 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e018e03c925c457c9b1edc1a72f0b001
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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