Boron tribromide → HCID 25149596、化合物

HRID 2108606ノート

反応式

HRID 2108606 の反応式
[I:1][C:2]1[CH:3]=[C:4]([OH:21])[CH:5]=[C:6]([I:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1.B(Br)(Br)Br>ClCCl>[I:1][C:2]1[CH:3]=[C:4]([OH:21])[CH:5]=[C:6]([I:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 25149595HCID 25149595、化合物

生成物 1

HCID 25149596HCID 25149596、化合物収率 66%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

To a stirred solution of 3,5-diiodo-4-(4′-methoxy-3′-iso-propylphenoxy)phenol (0.28 g, 0.55 mmol) in dichloromethane (17.0 mL) at −78° C. was added BBr3 (13.1 mL, 13.1 mmol, 1.0 M solution in CH2Cl2). The reaction mixture was stirred at −78° C. for 10 min, allowed to warm to room temperature and stirred for 16 h. The reaction mixture was poured into ice and extracted with CH2Cl2 (20 mL×2). The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with acetone-hexanes (3:7) to afford 3,5-diiodo-4-(4′-hydroxy-3′-iso-propylphenoxy)phenol as an off-white solid (0.18 g, 66%): 1H NMR (300 MHz, DMSO-d6): δ 9.95 (s, 1H), 8.91 (s, 1H), 7.27 (s, 2H), 6.62 (d, J=9.0 Hz, 1H), 6.56 (d, J=3.0 Hz, 1H), 6.18 (m, 1H), 3.72 (s, 3H), 3.14 (m, 1H), 1.10 (d, J=6.0 Hz, 6H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=hexanes-acetone (7:3); Rf=0.28.

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred for 16 h
  3. additionThe reaction mixture was poured into ice
  4. extractionextracted with CH2Cl2 (20 mL×2)
  5. dry with materialThe organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica gel
  9. washeluting with acetone-hexanes (3:7)

出典と根拠

ORDレコード
ord-721aeda33bc04974ac8cdbd25441fb80
出典データセット
uspto-grants-2009_04
特許番号
US07514419B2

反応ノート

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