Carbon tetrabromide → HCID 86718158, compound

HRID 570573Notes

Reaction equation

HRID 570573 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10]O)[CH:6]=[CH:5][N:4]=1.C(Br)(Br)(Br)[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[Br:13][CH2:10][CH2:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 15319874HCID 15319874, compound

Product 1

HCID 86718158HCID 86718158, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(2-methoxypyridin-4-yl)ethanol (commercially available) (700 mg, 4.57 mmol,), CBr4 (2.27 g, 6.85 mmol) and triphenylphosphine (1.8 g, 6.85 mmol) in 75 mL toluene was stirred at RT for 64 h. The mixture was filtered over a silica-plug and washed with toluene. The filtrate concentrated under vacuum to yield the crude product. The residue was purified by column chromatography on silica eluting with a gradient formed from heptane and EtOAc to yield, after evaporation of the product containing fraction, 624 mg (63%) of the title compound as colourless liquid. MS (m/e): 216.2 (MH+).

Workup

  1. filtrationThe mixture was filtered over a silica-plug
  2. washwashed with toluene
  3. concentrationThe filtrate concentrated under vacuum
  4. customto yield the crude product
  5. customThe residue was purified by column chromatography on silica eluting with a gradient
  6. customformed from heptane and EtOAc
  7. customto yield
  8. customafter evaporation of the product
  9. additioncontaining fraction, 624 mg (63%) of the title compound as colourless liquid

Sources & evidence

ORD record
ord-f29f97a153484db9b64a5367841e8cf0
Source dataset
uspto-grants-2015_05
Patent number
US09023852B2

Reaction notes

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