Carbon tetrabromide → 2'-(Bromomethyl)-4-fluoro-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl-3-ol

HRID 1028628ノート

反応式

HRID 1028628 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[F:25][C:26]1[C:31]([CH:32]([CH3:34])[CH3:33])=[CH:30][C:29]([C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][C:36]=2CO)=[C:28]([O:47][CH3:48])[C:27]=1[OH:49]>C(Cl)Cl>[Br:24][CH2:20][C:36]1[CH:37]=[C:38]([C:41]([F:44])([F:42])[F:43])[CH:39]=[CH:40][C:35]=1[C:29]1[CH:30]=[C:31]([CH:32]([CH3:34])[CH3:33])[C:26]([F:25])=[C:27]([OH:49])[C:28]=1[O:47][CH3:48]

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 866034354-Fluoro-2'-(hydroxymethyl)-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl-3-ol

生成物 1

HCID 866034362'-(Bromomethyl)-4-fluoro-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl-3-ol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of triphenylphosphine (102.8 mg, 0.392 mmol) in dry CH2Cl2 (2 mL) was added by cannula to a stirred solution of carbon tetrabromide (130 mg, 0.392 mmol) and 4-fluoro-2′-(hydroxymethyl)-5-isopropyl-2-methoxy-4′-(trifluoromethyl)biphenyl-3-ol (58.5 mg, 0.163 mmol) in dry CH2Cl2 (2 mL) at 0° C. under N2 and the reaction was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12×160 mm, 0-40% EtOAc in hexanes gradient) to afford 2′-(bromomethyl)-4-fluoro-5-isopropyl-2-methoxy-4′-(trifluoromethyl)biphenyl-3-ol. Rf=0.55 (20% EtOAc in hexanes). 1H NMR (600 MHz, CDCl3) δ 7.84 (s, 1H), 7.61 (d, J=7.9 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 6.69 (d, J=7.8 Hz, 1H), 5.59 (s, 1H), 4.50 (d, J=9.6 Hz, 1H), 4.39 (d, J=9.7 Hz, 1H), 3.47 (s, 3H), 3.29-3.23 (m, 1H), 1.27 (d, J=6.9 Hz, 6H).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give the crude product
  3. customThis was purified by flash chromatography (Si, 12×160 mm, 0-40% EtOAc in hexanes gradient)

出典と根拠

ORDレコード
ord-41cebcf78bc24598922d3bb1fddce26a
出典データセット
uspto-grants-2014_05
特許番号
US08735435B2

反応ノート

読み込み中…