Hydrochloric Acid → (3-Bromo-2-methylphenyl)methanol

HRID 14977

반응식

HRID 14977 반응식
C([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[C:5]([CH3:12])[C:4]=1[Br:13])C.CO.Cl>O1CCCC1>[Br:13][C:4]1[C:5]([CH3:12])=[C:6]([CH2:7][OH:8])[CH:10]=[CH:11][CH:3]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 67045088Ethyl 3-bromo-2-methylbenzoic acid2회

생성물 1

HCID 10035697(3-Bromo-2-methylphenyl)methanol수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl 3-bromo-2-methylbenzoic acid was reduced as follows: Add 5 equivalents of borane tetrahydrofuran complex, via syringe, to 10 mmol ethyl 3-bromo-2-methylbenzoic acid in tetrahydrofuran (5 mL). The mixture was refluxed for two hours, then cooled in an ice bath. Methanol (10 mL) was added dropwise, followed by 1 N HCl (50 mL). The solvent was removed and the mixture partitioned between ethyl acetate and water. The yield was 90%. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) 67.5 (d, 1H) 7.2 (d, 1H) 7.1 (t, 1H), 4.6 (s, 2H) 2.3 (s, 3H).

후처리

  1. additionAdd 5 equivalents of borane tetrahydrofuran complex
  2. temperatureThe mixture was refluxed for two hours
  3. temperaturecooled in an ice bath
  4. customThe solvent was removed
  5. customthe mixture partitioned between ethyl acetate and water

출처 및 근거

ORD 기록
ord-1c31d44872d04c0c869ef0842a3a3eab
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732444B2

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