Water → (4-Fluoro-2-methylphenyl)(4-fluorophenyl)methanol

HRID 561420ノート

反応式

HRID 561420 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH3:9].C([Li])CCC.[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1.O>O1CCCC1.CCCCCC.C(OCC)(=O)C>[F:8][C:5]1[CH:6]=[CH:7][C:2]([CH:20]([C:19]2[CH:22]=[CH:23][C:16]([F:15])=[CH:17][CH:18]=2)[OH:21])=[C:3]([CH3:9])[CH:4]=1

参加物

8

反応物 4

HCID 962WaterHCID 680234-FluorobenzaldehydeHCID 967432-Bromo-5-fluorotolueneHCID 178418339Butyllithium

生成物 1

HCID 58392149(4-Fluoro-2-methylphenyl)(4-fluorophenyl)methanol

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1.00 g (5.29 mmol) of 2-bromo-5-fluorotoluene were dissolved in 10 ml of tetrahydrofuran at −78° C. Addition of 4.0 ml (6.35 mmol) of a 1.6N solution of n-butyllithium in hexane was followed by stirring for 15 min, and then 0.79 g (6.35 mmol) of p-fluorobenzaldehyde dissolved in 10 ml of tetrahydrofuran was added dropwise. The mixture was warmed to RT and stirred for 1 h. The reaction solution was mixed with water and ethyl acetate, and the phases were separated. The aqueous phase was extracted three times with ethyl acetate, and the combined organic phases were washed with saturated aqueous sodium chloride solution. The solvents were removed in vacuo, and the crude product was purified by preparative HPLC (mobile phase: acetonitrile-water gradient). 0.56 g (43% of theory) of the title compound was obtained.

後処理

  1. additionwas added dropwise
  2. stirringstirred for 1 h
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted three times with ethyl acetate
  5. washthe combined organic phases were washed with saturated aqueous sodium chloride solution
  6. customThe solvents were removed in vacuo
  7. customthe crude product was purified by preparative HPLC (mobile phase: acetonitrile-water gradient)

出典と根拠

ORDレコード
ord-72a9b7629bdb48c7b48f8b0ed345465d
出典データセット
uspto-grants-2011_11
特許番号
US08063234B2

反応ノート

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