Carbon tetrabromide → 2-Nitrophenethyl bromide

HRID 459882

Reaction equation

HRID 459882 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.OC[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N+:34]([O-:36])=[O:35]>C(Cl)Cl>[Br:24][CH2:20][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N+:34]([O-:36])=[O:35]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 270542-Nitrophenethyl alcohol

Product 1

HCID 123638782-Nitrophenethyl bromideYield 80.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (39.2 g, 0.150 mol) and carbon tetrabromide (49.5 g, 0.150 mol) were added sequentially to a solution of 2-(2-hydroxyethyl)-nitrobenzene (25.0 g, 0.150 mol) in methylene chloride (400 mL) at 0° C. The reaction was stirred overnight and quenched with saturated sodium bicarbonate solution. The methylene chloride phase was washed with saturated brine and dried over magnesium sulfate. The crude product was treated with ethyl acetate, and the precipitated triphenylphosphine oxide removed by filtration. Further purification by flash chromatography by (silica gel, 0–10% ethyl acetate in hexane gradient elution) produced the title compound (27.9 g).

Workup

  1. customquenched with saturated sodium bicarbonate solution
  2. washThe methylene chloride phase was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. additionThe crude product was treated with ethyl acetate
  5. customthe precipitated triphenylphosphine oxide removed by filtration
  6. customFurther purification by flash chromatography
  7. washby (silica gel, 0–10% ethyl acetate in hexane gradient elution)

Sources & evidence

ORD record
ord-9e824795d08c4e0a87a527f40527cb19
Source dataset
uspto-grants-2007_03
Patent number
US07196079B2

Linked notes

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