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Bromide ion → 4-(3-Pyridylmethyloxymethyl)-2-phenylbenzoic acid methyl ester

HRID 2121157
Notes
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Reaction equation

HRID 2121157 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.[H-].[Na+].[CH3:11][O:12][C:13](=[O:28])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20]Br)=[CH:16][C:15]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Br-]>CN(C=O)C>[CH3:11][O:12][C:13](=[O:28])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][O:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:16][C:15]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 259Bromide ionHCID 75103-PyridinemethanolHCID 24758Sodium hydrideHCID 18474540Methyl 4-bromomethyl-2-phenylbenzoate

Product 1

HCID 540573764-(3-Pyridylmethyloxymethyl)-2-phenylbenzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

To a solution in DMF of 3-pyridinemethanol (0.59 mL) was added sodium hydride (60% in mineral oil, 0.19 g), and the mixture was stirred until gas evolution ceased. A solution of 2-phenyl-4-bromomethylbenzoic acid methyl ester (0.98 g) in DMF was then added and the reaction mixture was stirred until the bromide was consumed. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried, and concentrated. The residue was purified by chromatography on silica gel (1:1 ethyl acetate-hexanes) to give [4-(3-pyridylmethyloxymethyl)-2-phenylbenzoic acid methyl ester (0.58 g).

Workup

  1. customwas consumed
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (1:1 ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-4bdb8b511b7949efafc5baddc7a622f4
Source dataset
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06693123B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes