Ethyl bromoacetate → HCID 23522917, 화합물

HRID 392838

반응식

HRID 392838 반응식
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:8][C:9]1[CH:23]=[CH:22][C:12]([CH:13](Cl)[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1>ClCCl.[Zn].II>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][CH:13]([C:12]1[CH:22]=[CH:23][C:9]([F:8])=[CH:10][CH:11]=1)[C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1)[CH3:7]

참가 물질

6

반응물 2

HCID 7748Ethyl bromoacetateHCID 27237731,1'-(Chloromethylene)bis(4-fluorobenzene)

생성물 1

HCID 23522917HCID 23522917, 화합물수율 80%

시약·촉매·용매 3

HCID 807Iodine촉매HCID 23994Zinc촉매HCID 6344Dichloromethane용매3회

반응 조건

온도
2.5 °C

실험 절차

A suspension of zinc (5.7 g, 87.2 mmol) in dichloromethane (20 ml) was treated with iodine (0.1 g) and heated under reflux. A solution of ethyl bromoacetate (10.0 g, 59.8 mmol) in dichloromethane was then added dropwise over 15 min and the resulting mixture was heated for another 15 min. The thick paste was then cooled to 0-5° C. and treated dropwise with a solution of 4,4′-difluorobenzhydryl chloride (11.93 g, 50.0 mmol) in dichloromethane (20 ml). The cooling bath was then removed and the mixture was stirred at 22° C. for another 2 h. The reaction mixture was quenched by the addition of 1N hydrochloric acid and ethyl acetate. The organic phase was washed with water, saturated sodium bicarbonate, brine and dried (magnesium sulfate). Evaporation of the solvent under reduce pressure and distillation of the residue in vacuo gave 11.6 g (80%) of the title material as a clear oil: bp 95-100° C./0.1 torr (bulb to bulb distillation, air bath temperature). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.14 (3H, t, J=7.1 Hz, CH3), 3.01 (2H, d, J=8.1 Hz, CH2), 4.06 (2H, q, J=7.1 Hz, CH2), 4.54 (1H, t, J=8.1 Hz, CH),7.0 (4H, m, aromatics), 7.2 (4H, m, aromatics). Anal. Calcd for C17H16F2O2: C, 70.34; H, 5.56. Found: C, 70.44; H, 5.50.

후처리

  1. temperatureheated
  2. temperatureunder reflux
  3. temperaturethe resulting mixture was heated for another 15 min
  4. customThe cooling bath was then removed
  5. customThe reaction mixture was quenched by the addition of 1N hydrochloric acid and ethyl acetate
  6. washThe organic phase was washed with water, saturated sodium bicarbonate, brine
  7. dry with materialdried (magnesium sulfate)
  8. customEvaporation of the solvent
  9. distillationpressure and distillation of the residue in vacuo

출처 및 근거

ORD 기록
ord-3b7fadbd34d145cca383ec0875ab3117
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06803378B2

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