2-Bromo-5-(trifluoromethyl)benzaldehyde → 1-(2-Bromo-5-(trifluoromethyl)phenyl)ethanol

HRID 1473341ノート

反応式

HRID 1473341 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:14][Mg]Cl>C1COCC1.O>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:6][C:3]=1[CH:4]([OH:5])[CH3:14]

参加物

5

反応物 2

HCID 70180472-Bromo-5-(trifluoromethyl)benzaldehydeHCID 178418332HCID 178418332、化合物

生成物 1

HCID 574587951-(2-Bromo-5-(trifluoromethyl)phenyl)ethanol収率 98%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

To a solution of 2-bromo-5-(trifluoromethyl)benzaldehyde (10 g, 39.6 mmol) in THF (40 mL), methyl magnesium chloride (3 M in THF) (26.4 mL, 79.3 mmol) was added at −78° C. dropwise. The reaction was warmed to 25° C. and stirred at this temperature for 1 h under a nitrogen atmosphere. Then the reaction mixture was diluted with water (200 mL) extracted with ethyl acetate (2×200 mL). Organic part was dried over sodium sulfate, filtered and concentrated in vacuum to give the crude compound which was further purified by column chromatography using silica gel (100 to 200 mesh) eluting with 0% to 10% ethyl acetate in hexanes to afford 1-(2-bromo-5-(trifluoromethyl)phenyl)ethanol (10.4 g, 98%) as a clear liquid. MS (ESI, Negative ion) m/z (M−1): 267.0. 1H NMR (400 MHz, DMSO) δ 7.87 (s, 1H), 7.80 (d, J=8.2 Hz, 1H), 7.55 (d, J=8.0 Hz, 1H), 5.68 (d, J=4.2 Hz, 1H), 5.03-4.94 (m, 1H), 1.32 (d, J=6.3 Hz, 3H).

後処理

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. dry with materialOrganic part was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customto give the crude compound which
  6. customwas further purified by column chromatography
  7. washeluting with 0% to 10% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-1f6f4121210a4af6b0e608009c920879
出典データセット
uspto-grants-2015_04
特許番号
US09012443B2

反応ノート

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