Hydrochloric Acid → (3-Bromo-4-methylphenyl)methanol

HRID 2386570

반응식

HRID 2386570 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:5](OCC)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:10]=[CH:11][C:12]=1[CH3:13]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14945865Ethyl 3-bromo-4-methylbenzoate2회HCID 21226445Aluminium lithium hydride2회

생성물 1

HCID 12947381(3-Bromo-4-methylphenyl)methanol수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

Ethyl 3-bromo-4-methylbenzoate was reduced follows: 2 equivalents lithium aluminium hydride (LAH) in THF was cooled to 0° C. Ethyl 3-bromo-4-methylbenzoate in anhydrous THF (10 mL) was added slowly to the cooled solution of LAH over 10 minutes, while stirring. The mixture was stirred at room temperature for 1 hour. The reaction was cooled to 0° C. and poured into ether (100 mL). The mixture was acidified by adding 1N HCl (aqueous) dropwise over 10 minutes. Separate fractions and wash aqueous phase with ether (50 mL). The fractions were combined and dried over magnesium sulfate. Solvent removal left a clear oil. The yield was 90%. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 7.5 (s, 1H) 7.2 (d, 1H) 7.1 (d, 1H), 4.6 (s, 2H) 2.3 (s, 3H).

후처리

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. washSeparate fractions and wash aqueous phase with ether (50 mL)
  3. dry with materialdried over magnesium sulfate
  4. customSolvent removal
  5. waitleft a clear oil

출처 및 근거

ORD 기록
ord-f39c85868f804b84807b64b5a1304860
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268822B2

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