Hydrochloric Acid → Tert-butyl 3-(4-bromophenyl)-2,2-dimethylpropionate

HRID 1266500노트

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HRID 1266500 반응식
C([N-]C(C)C)(C)C.[Li+].[CH3:9][CH:10]([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1.Cl>O1CCCC1>[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][C:10]([CH3:18])([CH3:9])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:22][CH:21]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 685274-Bromobenzyl bromideHCID 519334Tert-butyl 2-methylpropanoateHCID 2724682Lithium diisopropylamide

생성물 1

HCID 22708227Tert-butyl 3-(4-bromophenyl)-2,2-dimethylpropionate수율 85%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

At −78° C., 34.7 ml (69.4 mmol) of a 2 M lithium diisopropylamide solution are slowly added dropwise to a solution of 10.0 g (69.34 mmol) of tert-butyl 2-methylpropionate (Example I-1) in 100 ml of tetrahydrofuran. After the addition has ended, the mixture is stirred at −78° C. for 1 h, and a solution of 15.76 g (63.04 mmol) of 4-bromobenzyl bromide in 10 ml of tetrahydrofuran is then added and the mixture is stirred at −78° C. for 1 h. The reaction is then warmed to room temperature and poured into 100 ml of 1 N hydrochloric acid, the phases are separated and the aqueous phase is extracted 3× with diethyl ether. The combined organic phases are washed with NaHCO3 solution, dried over sodium sulphate and freed from the solvent under reduced pressure. Distillative purification of the residue under oil pump vacuum gives 16.75 g (85%) of tert-butyl 3-(4-bromophenyl)-2,2-dimethylpropionate.

후처리

  1. customAt −78° C.
  2. additionAfter the addition
  3. stirringthe mixture is stirred at −78° C. for 1 h
  4. temperatureThe reaction is then warmed to room temperature
  5. customthe phases are separated
  6. extractionthe aqueous phase is extracted 3× with diethyl ether
  7. washThe combined organic phases are washed with NaHCO3 solution
  8. dry with materialdried over sodium sulphate
  9. distillationDistillative purification of the residue under oil pump vacuum

출처 및 근거

ORD 기록
ord-c1e729df75fb4184a9790a9764544f2f
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06548538B2

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