Methanol → 2-Bromo-1,3-dimethoxy-5-(methoxymethyl)benzene

HRID 347865

반응식

HRID 347865 반응식
S(Cl)(C)(=O)=O.[Br:6][C:7]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH2:15][OH:16])=[CH:9][C:8]=1[O:17][CH3:18].[CH2:19](N(CC)CC)C.C[O-].[Na+].CO>COCCOC.O.C1(C)C=CC=CC=1>[Br:6][C:7]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH2:15][O:16][CH3:19])=[CH:9][C:8]=1[O:17][CH3:18]

참가 물질

9

반응물 5

HCID 887MethanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10942334Sodium MethoxideHCID 11149289(4-Bromo-3,5-dimethoxyphenyl)methanol

생성물 1

HCID 230809402-Bromo-1,3-dimethoxy-5-(methoxymethyl)benzene수율 99.5%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 80711,2-Dimethoxyethane용매

실험 절차

Mesyl chloride (34.5 mL, 446 mmol) was added to a solution of (4-bromo-3,5-dimethoxyphenyl)methanol (100 g, 405 mmol) and triethylamine (67.5 mL, 484 mmol) in 1.2-dimethoxyethane (1000 mL) while cooling with ice, and the reaction mixture was stirred for 30 minutes. After adding a 28% sodium methoxide in methanol (350 mL, 1.72 mol) to the reaction mixture, it was further stirred for 3 hours at room temperature. Upon completion of the reaction, toluene (1000 mL) and water (1000 mL) were added to the reaction mixture, the aqueous layer was removed, and the organic extract was washed with water (1000 mL), 1N hydrochloric acid (500 mL) and water (500 mL) in that order and concentrated under reduced pressure to afford 105 g of the title compound as a colorless oil (99.5% yield).

후처리

  1. temperaturewhile cooling with ice
  2. stirringwas further stirred for 3 hours at room temperature
  3. additionwere added to the reaction mixture
  4. customthe aqueous layer was removed
  5. extractionthe organic extract
  6. washwas washed with water (1000 mL), 1N hydrochloric acid (500 mL) and water (500 mL) in that order
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-010d34d98dd24f95b563cc8a7cdee595
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176216B2

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