Hydrochloric Acid → 2-Benzyl-4-bromophenol

HRID 25827

반응식

HRID 25827 반응식
[Al+3].[Cl-].[Cl-].[Cl-].[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH:19](O)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]=1.Cl>CCOCC.C(Cl)Cl.CCOCC.CO>[CH2:19]([C:14]1[CH:13]=[C:12]([Br:11])[CH:17]=[CH:16][C:15]=1[OH:18])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 121347074-Bromo-2-(hydroxy-phenyl-methyl)-phenolHCID 21226445Aluminium lithium hydride

생성물 1

HCID 134735702-Benzyl-4-bromophenol수율 62%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매3회HCID 6344Dichloromethane용매HCID 21864698Diethyl ether methanol용매

실험 절차

A solution of 13.24 g (99.3 mmol, 4.1 eqv) AlCl3 in 85 ml dry Et2O was added cautiously under stirring to a suspension of 3.91 g (102.9 mmol, 4.2 eqv) LiAlH4 in 100 ml dry Et2O. After complete addition the resulting mixture was stirred for 30 min at rt and then a solution of 6.85 g (24.5 mmol) 4-Bromo-2-(hydroxy-phenyl-methyl)-phenol (19) in 80 ml dry Et2O was added dropwise. The mixture was refluxed for 12 h and after that cooled to 0° C. After adding cautiously 60 ml of a mixture of Et2O/MeOH (1:1), 170 ml 1 N HCl-solution was added and the mixture was extracted with Et2O. The comb. org. fractions were washed with brine, dried over Na2SO4 and evaporated. Column chromatography (CH2Cl2) yielded 4.00 g (15.2 mmol, 62%) 20 as a colorless liquid: Rf (CH2Cl2) 0.41; 1H NMR (500 MHz, CDCl3) δ 3.95 (s, 2H), 4.64 (s, 1H), 6.67 (dd, 1H, J1=8.04 Hz, J2=0.79 Hz), 7.23 (m, 5H), 7.31 (m, 2H); LRMS (EI) m/z 265 (17), 264 (98), 263 (21), 262 (100), 186 (53), 184 (49), 183 (78), 182 (18), 181 (27), 165 (49), 153 (23), 152 (26), 91 (29), 84 (14), 78 (25), 77 (31), 76 (16), 63 (15); HRMS (EI) Calcd. for C13H11BrO: 261.999326. Found: 261.998568.

후처리

  1. additionAfter complete addition the resulting mixture
  2. temperatureThe mixture was refluxed for 12 h
  3. temperatureafter that cooled to 0° C
  4. additionwas added
  5. extractionthe mixture was extracted with Et2O
  6. washfractions were washed with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated

출처 및 근거

ORD 기록
ord-016c65ea75374e289a6a4040944a0b26
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858600B2

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