Nitric Acid → 2-Bromo-4-(bromomethyl)-1-methoxybenzene

HRID 1632055ノート

反応式

HRID 1632055 の反応式
[Br-:1].[K+].[N+]([O-])(O)=O.[Br:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.ClC(Cl)C>[Br:1][C:13]1[CH:14]=[C:9]([CH2:8][Br:7])[CH:10]=[CH:11][C:12]=1[O:15][CH3:16]

参加物

6

反応物 3

HCID 944Nitric AcidHCID 1650214-Methoxybenzyl bromideHCID 253877Potassium Bromide

生成物 1

HCID 112774622-Bromo-4-(bromomethyl)-1-methoxybenzene収率 26.6%

試薬・触媒・溶媒 2

HCID 70681Tetrabutylammonium Chloride触媒HCID 63651,1-Dichloroethane溶媒2 回

実験手順

To solution of potassium bromide (29.6 g, 248 mmol) in nitric acid (21% by volume, 149 g, 497 mmol), was added dichloroethane (188 mL) and tetrabutylammonium chloride (1.04 g, 3.73 mmol) followed by 4-(bromomethyl)anisol (25.0 g, 124 mmol) in dichloroethane (62 mL), and the reaction was stirred at room temperature for 5 h. The organic layer was separated, washed with water (2×100 mL, 2×150 mL), 2% aqueous potassium carbonate (150 mL), dried over sodium sulfate, and the solvent removed under vacuum. The residue was purified by being run through a flash silica gel plug (10% ethyl acetate in hexanes) to give the title compound (I-42) (9.22 g, 26% yield). 1H NMR (400 MHz, CDCl3) δ: 7.59 (d, 1H), 7.30 (dd, J=8.2, 2.2 Hz, 1H), 6.85 (d, J=8.4 Hz, 1H), 4.44 (s, 2H), 4.44 (s, 3H).

後処理

  1. customThe organic layer was separated
  2. washwashed with water (2×100 mL, 2×150 mL), 2% aqueous potassium carbonate (150 mL)
  3. dry with materialdried over sodium sulfate
  4. customthe solvent removed under vacuum
  5. customThe residue was purified

出典と根拠

ORDレコード
ord-6313d8867f1e488aa72459607702e2f7
出典データセット
uspto-grants-2014_07
特許番号
US08791267B2

反応ノート

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