3-Methoxytoluene → (4-Bromophenyl)[2-methyl-4-(methyloxy)phenyl]methanone

HRID 229148

反応式

HRID 229148 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][C:12]1[CH:13]=[C:14]([O:18][CH3:19])[CH:15]=[CH:16][CH:17]=1.[Al+3].[Cl-].[Cl-].[Cl-]>O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:17]2[CH:16]=[CH:15][C:14]([O:18][CH3:19])=[CH:13][C:12]=2[CH3:11])=[O:7])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 75303-MethoxytolueneHCID 685154-Bromobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 11023132(4-Bromophenyl)[2-methyl-4-(methyloxy)phenyl]methanone収率 73%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of 4-bromobenzoyl chloride (1.12 g, 5.12 mmol) and 3-methyl anisole (1.95 mL, 15.47 mmol) at 0° C. was added AlCl3 (0.83 g, 6.20 mmol). The mixture was allowed to warm to RT over 12 h with stirring. Water was added slowly, and the mixture was extracted with CH2Cl2. The organics were dried with MgSO4 and concentrated. The crude material was purified by chromatography on silica gel (EtOAc:hexanes) to yield 1.14 g (73%) of compound 27. 1H NMR (400 MHz, CDCl3): δ 2.41 (s, 3H), 3.86 (s, 3H), 6.74 (dd, J=2.5 Hz, 8.6 Hz, 1H), 6.82 (d, J=2.6 Hz, 1H), 7.31 (d, J=8.6 Hz, 1H), 7.58 (d, J=8.5 Hz, 2H), 7.62 (d, J=8.5 Hz, 2H).

後処理

  1. extractionthe mixture was extracted with CH2Cl2
  2. dry with materialThe organics were dried with MgSO4
  3. concentrationconcentrated
  4. customThe crude material was purified by chromatography on silica gel (EtOAc:hexanes)

出典と根拠

ORDレコード
ord-c25237681b384baa81e76366647fb27b
出典データセット
uspto-grants-2009_07
特許番号
US07560589B2

関連ノート

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