Carbon tetrabromide → Pyridine, 2-(bromomethyl)-6-(difluoromethoxy)-

HRID 594305Notes

Reaction equation

HRID 594305 reaction equation
[F:1][CH:2]([F:12])[O:3][C:4]1[N:9]=[C:8]([CH2:10]O)[CH:7]=[CH:6][CH:5]=1.C(Br)(Br)(Br)[Br:14].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:14][CH2:10][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([O:3][CH:2]([F:12])[F:1])[N:9]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 69083466[6-(Difluoromethoxy)pyridin-2-yl]methanol

Product 1

HCID 69082287Pyridine, 2-(bromomethyl)-6-(difluoromethoxy)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (6-(difluoromethoxy)pyridin-2-yl)methanol (250 mg; 1.42 mmol) in anh. DCM (12 ml) was treated at rt with CBr4 (473 mg; 1.42 mmol), and with PPh3 (374 mg; 1.42 mmol). The resulting mixture was further stirred at rt, under nitrogen, for 1 h. Concentration to dryness under reduced pressure, and subsequent purification by FC (DCM) afforded 2-(bromomethyl)-6-(difluoromethoxy)pyridine as a yellow oil which was directly used for the next reaction. LC-MS (conditions D): tR=0.95 min.; [M+H]+: 237.82 g/mol.

Workup

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

Sources & evidence

ORD record
ord-44728ec98ec64f56bc4d4d90520694a4
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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