2,2,2-Trifluoro-1-methoxyethanol → 6-bromo-4,4-dimethyl-2-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazine

HRID 277867

反応式

HRID 277867 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([OH:12])([CH3:11])[CH3:10].CO[CH:15](O)[C:16]([F:19])([F:18])[F:17].S([O-])([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][CH:15]([C:16]([F:19])([F:18])[F:17])[O:12][C:9]([CH3:10])([CH3:11])[C:3]=2[CH:4]=1

参加物

5

反応物 3

HCID 98922,2,2-Trifluoro-1-methoxyethanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 120422752-(2-Amino-5-bromophenyl)propan-2-ol

生成物 1

HCID 234355726-bromo-4,4-dimethyl-2-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazine

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2-(2-amino-5-bromo-phenyl)-propan-2-ol (5 g, 21.7 mmol), trifluoroacetaldehyde methyl hemiacetal (5 mL), and magnesium sulfate (10 g) in toluene (75 mL) was heated at 80° C. under nitrogen. After disappearance of the starting material, the reaction was filtered through a pad of silica gel and the filtrate dried over sodium sulfate and concentrated to give 6-bromo-4,4-dimethyl-2-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazine as an amorphous solid: 1H-NMR (DMSO-d6) δ 7.31 (d, 1H, J=1.99 Hz), 7.19 (dd, 1H, J=8.73, 2.38 Hz), 6.88 (s, 1H), 6.74 (d, 1H, J=8.33 Hz), 5.32 (m, 1H), 1.52 (s, 6H).

後処理

  1. filtrationAfter disappearance of the starting material, the reaction was filtered through a pad of silica gel
  2. dry with materialthe filtrate dried over sodium sulfate
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-a1ac86a113da49aa8e9fce5c94023f0f
出典データセット
uspto-grants-2002_03
特許番号
US06358948B1

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