Carbon tetrabromide → 2-Nitrophenethyl bromide

HRID 1695885Notes

Reaction equation

HRID 1695885 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:33]>C(Cl)Cl>[Br:33][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 270542-Nitrophenethyl alcohol

Product 1

HCID 123638782-Nitrophenethyl bromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-hydroxyethyl)-2-nitrobenzene (21 ml, 150 mmol) and triphenylphosphine (39.2 g, 150 mmol) in DCM (400 ml) at 0° C. was add CBr4 (49.5 g, 150 mmol) in portions and the reaction mixture was stirred from 0° C. to RT overnight. The reaction mixture was quenched with sat. aq. Na2CO3, the layers were separated and the organic layer was washed with brine, dried (MgSO4) and evaporated to dryness. The residue was treated with EtOAc and the precipitated Ph3O was filtered and the solvent removed. This was repeated twice more. Purification by column chromatography (0% to 10% EtOAc in Hx) gave an oil that solidified on standing.

Workup

  1. customThe reaction mixture was quenched with sat. aq. Na2CO3
  2. customthe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. additionThe residue was treated with EtOAc
  7. filtrationthe precipitated Ph3O was filtered
  8. customthe solvent removed
  9. customPurification by column chromatography (0% to 10% EtOAc in Hx)
  10. customgave an oil that

Sources & evidence

ORD record
ord-a6f5adad39094a849c5e69f6dd0bcdf8
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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