Carbon tetrabromide → 2-Nitrophenethyl bromide

HRID 459882

반응식

HRID 459882 반응식
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]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 270542-Nitrophenethyl alcohol

생성물 1

HCID 123638782-Nitrophenethyl bromide수율 80.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9e824795d08c4e0a87a527f40527cb19
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196079B2

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