Water → HCID 68689230, compound

HRID 1175210Notes

Reaction equation

HRID 1175210 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10](I)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Cl-].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Zn+].O>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 962WaterHCID 21942573Methyl 3-bromo-5-iodobenzoateHCID 178479831HCID 178479831, compound

Product 1

HCID 68689230HCID 68689230, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To an argon purged solution of methyl 3-bromo-5-iodobenzoate (834 mg, 2.45 mmol) and Pd(PPh3)4 (142 mg, 0.12 mmol) in THF (20 mL) was added 2-pyridylzinc chloride (0.5 M, 7.4 mL, 3.7 mmol). The mixture was stirred overnight and then poured into a large volume of water (100 mL). The resulting solution was extracted with EtOAc (3×20 mL) and the combined organics were successively washed with water (1×20 mL), brine (1×20 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified via automated flash chromatography (silica gel; 0 to 25% EtOAc in hexanes) to afford methyl 3-bromo-5-(pyridin-2-yl)benzoate. MS m/z=292, 294 [M+1]+; Calc'd for C13H10BrNO2: 292.

Workup

  1. extractionThe resulting solution was extracted with EtOAc (3×20 mL)
  2. washthe combined organics were successively washed with water (1×20 mL), brine (1×20 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified

Sources & evidence

ORD record
ord-88bda2710adb480fb096435ecb0cbfa0
Source dataset
uspto-grants-2010_11
Patent number
US07838676B2

Reaction notes

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