Carbon tetrabromide → HCID 90203452, compound

HRID 1480057Notes

Reaction equation

HRID 1480057 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[C:5]([Cl:10])=[CH:4][N:3]=1.[Br:11]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:11][CH2:8][C:6]1[C:5]([Cl:10])=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1480674(2,5-dichloropyridin-4-yl)methanol

Product 1

HCID 90203452HCID 90203452, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 2,5-dichloro-4-pyridinemethanol (CAN 866039-42-1, 1.10 g, 6.18 mmol) in DCM (25 mL) was added at 0° C. with stirring tetrabromomethane (2.05 g, 6.18 mmol) and a solution of triphenylphosphine (1.62 g, 6.18 mmol) in DCM (5 mL). The resulting mixture was stirred at 0° C. for 1 h and concentrated. The residue was purified by flash chromatography (silica, heptane/ethyl acetate gradient) to give the title compound (619 mg, 42%) as yellow oil. LC-MS (UV peak area, m/z) 98%, 241.0 (MH+).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography (silica, heptane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-991eca45e8a84ea696d0e132e31dab7e
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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