4-Fluorophenol → 3-Bromo-4-(4-fluoro-phenoxymethyl)-pyridine

HRID 712643Notes

Reaction equation

HRID 712643 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][OH:9].[F:10][C:11]1[CH:16]=[CH:15][C:14](O)=[CH:13][CH:12]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][O:9][C:14]1[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 46840038(3-Bromopyridin-4-yl)methanol

Product 1

HCID 1055225733-Bromo-4-(4-fluoro-phenoxymethyl)-pyridineYield 92.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (3-bromo-pyridin-4-yl)-methanol (650 mg, 3.5 mmol), 4-fluoro-phenol (260 mg, 2.3 mmol) and PPh3 (1.7 g, 6.4 mmol) in THF (50 mL) is added a solution of di-tert-butyl azodicarboxylate (1.2 g, 5 mmol) in THF at 0° C. After addition, the mixture is stirred at room temperature for 16 hrs. The solvent is removed and the residue is purified by flash column chromatography to give 600 mg of 3-bromo-4-(4-fluoro-phenoxymethyl)-pyridine.

Workup

  1. additionAfter addition
  2. customThe solvent is removed
  3. customthe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-b42b9c15716c469cb92d83729e46e17a
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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