Carbon tetrabromide → 5-(Bromomethyl)-2-(difluoromethoxy)pyridine

HRID 594299Notes

Reaction equation

HRID 594299 reaction equation
[F:1][CH:2]([F:12])[O:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10]O)=[CH:6][CH:5]=1.C(Br)(Br)(Br)[Br:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:14][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][CH:2]([F:12])[F:1])=[N:9][CH:8]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 69085050(6-(Difluoromethoxy)pyridin-3-yl)methanol

Product 1

HCID 690853875-(Bromomethyl)-2-(difluoromethoxy)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (6-(difluoromethoxy)pyridin-3-yl)methanol (246 mg; 1.41 mmol) in anh. DCM (10 ml) was treated at rt with CBr4 (467 mg; 1.41 mmol), and with triphenylphosphine (369 mg; 1.41 mmol). The resulting mixture was further stirred at rt, under nitrogen, for 15 h. Concentration to dryness under reduced pressure, and subsequent purification by FC (DCM) afforded 5-(bromomethyl)-2-(difluoromethoxy)pyridine as an orange oil which was directly used for the next reaction.

Workup

  1. concentrationConcentration to dryness
  2. customunder reduced pressure, and subsequent purification by FC (DCM)

Sources & evidence

ORD record
ord-8c73e791e87745f0a7e9789d18ec12ae
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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