18-Crown-6 → 2-[(5-Bromo-4-fluoro-2-nitrophenyl)oxy]-1-chloro-3-fluoro-4-methylbenzene

HRID 1875198

反応式

HRID 1875198 の反応式
[Cl:1][C:2]1[C:7]([OH:8])=[C:6]([F:9])[C:5]([CH3:10])=[CH:4][CH:3]=1.C1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+].[Br:35][C:36]1[CH:41]=[C:40](F)[C:39]([N+:43]([O-:45])=[O:44])=[CH:38][C:37]=1[F:46]>CS(C)=O.CCOC(C)=O>[Br:35][C:36]1[C:37]([F:46])=[CH:38][C:39]([N+:43]([O-:45])=[O:44])=[C:40]([O:8][C:7]2[C:6]([F:9])=[C:5]([CH3:10])[CH:4]=[CH:3][C:2]=2[Cl:1])[CH:41]=1

参加物

7

反応物 4

HCID 2855718-Crown-6HCID 27362864-Bromo-2,5-difluoronitrobenzeneHCID 27736846-Chloro-2-fluoro-3-methylphenolHCID 23665647Potassium tert-butoxide

生成物 1

HCID 684871652-[(5-Bromo-4-fluoro-2-nitrophenyl)oxy]-1-chloro-3-fluoro-4-methylbenzene収率 71%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 6-chloro-2-fluoro-3-methylphenol (12.8 g, 80 mmol) and 18-crown-6 (4.21 g, 15.94 mmol) in DMSO (100 ml) at 0° C. was added potassium tert-butoxide (1.0 M solution in THF) (80 ml, 80 mmol) and the reaction mixture was stirred at RT for 30 minutes. Next, 1-bromo-2,5-difluoro-4-nitrobenzene (19.4 g, 80 mmol) was added dropwise (in solution of 60 mL DMSO) and the reaction mixture was stirred overnight at RT. The reaction mixture was diluted with EtOAc and washed with water. The solvent was removed and the crude material was triturated with methanol to give 2-[(5-bromo-4-fluoro-2-nitrophenyl)oxy]-1-chloro-3-fluoro-4-methylbenzene (21.3 g, 56.3 mmol, 71% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.26 (d, 1H), 7.34-7.40 (m, 1H), 7.21-7.34 (m, 2H), 2.23 (d, 3H).

後処理

  1. stirringthe reaction mixture was stirred overnight at RT
  2. washwashed with water
  3. customThe solvent was removed
  4. customthe crude material was triturated with methanol

出典と根拠

ORDレコード
ord-aff3195a2bac40af98de59828479ad8d
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

関連ノート

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