Carbon tetrabromide → 2-(Bromomethyl)-4-(difluoromethoxy)pyridine

HRID 594308Notes

Reaction equation

HRID 594308 reaction equation
[F:1][CH:2]([F:12])[O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:10]O)[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:6]1[CH:5]=[C:4]([O:3][CH:2]([F:12])[F:1])[CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 69082615(4-(Difluoromethoxy)pyridin-2-yl)methanol

Product 1

HCID 690801602-(Bromomethyl)-4-(difluoromethoxy)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (4-(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)-4-(difluoromethoxy)pyridine as a yellow oil which was directly used for the next reaction. LC-MS (conditions A): tR=0.56 min.; [M+H]+: 237.92 g/mol.

Workup

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

Sources & evidence

ORD record
ord-23b028bf89f54aabae123c67689ba62e
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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