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

HRID 347865ノート

反応式

HRID 347865 の反応式
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]

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-010d34d98dd24f95b563cc8a7cdee595
出典データセット
uspto-grants-2007_02
特許番号
US07176216B2

反応ノート

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