N-bromobutanimide → 6-(2-Bromomethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester

HRID 1094510Notes

Reaction equation

HRID 1094510 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([CH3:22])[N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4].[Br:23]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([CH2:22][Br:23])[N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 666401866-(2-Methyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester

Product 1

HCID 666399346-(2-Bromomethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 8.55 g (29.05 mMol) 6-(2-methyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester, 13.5 g N-bromo-succinimide (95%; 72.6 mMol) and 3.31 g (20 mMol) α,α-azoisobytyronitrile in 1.85 l CCl4 is heated to 80° C. and irradiated (125 W lamp) for 2 days. Then 5.44 g N-bromo-succinimide and 1.66 g α,α-azoisobytyronitrile are added and irradiation at 80° C. is continued for another day. The reaction mixture is concentrated, the residue re-dissolved in EtOAc and water, the aq. layer separated off and extracted with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; hexane/EtOAc 1:1) gives the title compound: MS: [M+1]+=373/375; TLC(hexane/EtOAc 1:1): Rf=0.35.

Workup

  1. customirradiated (125 W lamp) for 2 days
  2. customirradiation at 80° C.
  3. waitis continued for another day
  4. concentrationThe reaction mixture is concentrated
  5. dissolutionthe residue re-dissolved in EtOAc
  6. customwater, the aq. layer separated off
  7. extractionextracted with EtOAc
  8. washThe organic layers are washed with water and brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-93ec2ecdbd1848fd8d7604a414b6767d
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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