Diiodomethane → 2-Iodo-5-(trifluoromethyl)benzonitrile

HRID 537961ノート

反応式

HRID 537961 の反応式
N[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5].[I:14]CI.N(OC(C)(C)C)=O>C(#N)C.CCOCC>[I:14][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5]

参加物

6

反応物 3

HCID 6346DiiodomethaneHCID 10906Tert-Butyl nitriteHCID 126273614-Amino-3-cyanobenzotrifluoride2 回

生成物 1

HCID 533636442-Iodo-5-(trifluoromethyl)benzonitrile

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
35 °C

実験手順

To a solution of 2-amino-5-(trifluoromethyl)benzonitrile (Intermediate 7, 15.1 g) and diiodomethane (24 mL) in acetonitrile (150 mL) at 35° C. was added t-butyl nitrite (21 mL) dropwise. The reaction was maintained at approximately 35° C. during the addition. The reaction was aged for 30 min and then heated to 60° C. for 30 minutes. The reaction mixture was cooled, diluted with ether and washed twice with water, twice with aqueous sodium bisulfite, water and then brine. The solution was dried over anhydrous MgSO4, filtered through a silica gel plug and then concentrated giving afford a red oil. The product was purified by silica gel chromatography eluting sequentially with hexanes, 3:1 hexanes/CH2Cl2 and 1:1 hexanes/CH2Cl2 to afford 2-iodo-5-(trifluoromethyl)benzonitrile. 1H NMR (CDCl3, 500 MHz) δ 8.10 (d, J=8.5 Hz, 1H), 7.85 (d, J=1.8 Hz, 1H), 7.52 (dd, J=8.5, 1.8 Hz, 1H).

後処理

  1. temperatureheated to 60° C. for 30 minutes
  2. temperatureThe reaction mixture was cooled
  3. washwashed twice with water, twice with aqueous sodium bisulfite, water
  4. dry with materialThe solution was dried over anhydrous MgSO4
  5. filtrationfiltered through a silica gel plug
  6. concentrationconcentrated
  7. customgiving
  8. customafford a red oil
  9. customThe product was purified by silica gel chromatography
  10. washeluting sequentially with hexanes, 3:1 hexanes/CH2Cl2 and 1:1 hexanes/CH2Cl2

出典と根拠

ORDレコード
ord-e3cdabdf7d7c47ccae10ba347c6b8ba0
出典データセット
uspto-grants-2014_10
特許番号
US08865707B2

反応ノート

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