Sodium Hydroxide → 3-Iodo-5-(trifluoromethyl)benzaldehyde

HRID 217502

反応式

HRID 217502 の反応式
[I:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1)[CH:12]=[O:13]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 192615723-Iodo-5-(trifluoromethyl)benzyl alcohol

生成物 1

HCID 534147093-Iodo-5-(trifluoromethyl)benzaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of [3-iodo-5-(trifluoromethyl)phenyl]methanol (287 mg, 0.95 mmol) in CH2Cl2 (10 mL) was cooled to 0° C. and then Dess-Martin periodinane (604 mg, 1.42 mmol) was added. The reaction was slowly warmed to room temperature. After stirring at room temperature for twenty minutes, the reaction was poured into 1N NaOH (25 mL). The mixture was extracted with EtOAc (50 mL) and the organic extracts were washed with brine (25 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 0% to 10% EtOAc/hexanes afforded 3-iodo-5-(trifluoromethypbenzaldehyde. Rf=0.54 (15% EtOAc/hexanes). 1H NMR (CDCl3, 600 MHz) δ 9.98 (s, 1H), 8.39 (s, 1H), 8.19 (s, 1H), 8.09 (s, 1H).

後処理

  1. extractionThe mixture was extracted with EtOAc (50 mL)
  2. washthe organic extracts were washed with brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography with 0% to 10% EtOAc/hexanes
  7. customafforded 3-iodo-5-(trifluoromethypbenzaldehyde

出典と根拠

ORDレコード
ord-3ff2b1f71e1e4df9b60fabb2eb55bc9e
出典データセット
uspto-grants-2012_06
特許番号
US08193365B2

関連ノート

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