Water → HCID 46205449, compound

HRID 415143Notes

Reaction equation

HRID 415143 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)CCC.Br[C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([F:31])[CH:22]=1.O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[F:31][C:23]1[CH:22]=[C:21]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)[CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 6077842-(Tributylstannyl)pyridineHCID 113453114-Bromo-2-fluoro-benzoic acid methyl ester

Product 1

HCID 46205449HCID 46205449, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(Tributylstannyl)pyridine (11.2 g, 30.4 mmol) was dissolved in toluene (240 mL), methyl 4-bromo-2-fluorobenzoate (7.4 g, 33.4 mmol) and tetrakis(triphenyl-phosphine) Pd (1.75 g) were added thereto. The mixture was poured into water, extraction was carried out with ethyl acetate, the organic phase was dried and the solvent was evaporated. The residue was purified by column chromatography (silica gel, petroleum ether:ethyl acetate 50:1 to 10:1) to give methyl 2-fluoro-4-(pyridin-2-yl)benzoate (2.5 g, yield 35%). 1H-NMR (400 MHz, CDCl3) δ (ppm): 3.93 (s, 3H), 7.31-7.34 (m, 1H), 7.76-7.85 (m, 4H), 8.05 (t, J=7.6 Hz, 1H), 8.72-8.74 (m, 1H); LC-MS (ESI) m/z: 232 (M+1)+.

Workup

  1. customthe organic phase was dried
  2. customthe solvent was evaporated
  3. customThe residue was purified by column chromatography (silica gel, petroleum ether:ethyl acetate 50:1 to 10:1)

Sources & evidence

ORD record
ord-67e8bde2def04505a20455592bd509d8
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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