Methanol → 4'-Acetoxy-3-fluoro-5-hydroxystilbene

HRID 2236346ノート

反応式

HRID 2236346 の反応式
B(Br)(Br)Br.C([O:12][C:13]1[CH:14]=[C:15]([F:31])[CH:16]=[C:17]([CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28](=[O:30])[CH3:29])=[CH:23][CH:22]=2)[CH:18]=1)C1C=CC=CC=1.CO>C(Cl)Cl>[C:28]([O:27][C:24]1[CH:25]=[CH:26][C:21]([CH:20]=[CH:19][C:17]2[CH:18]=[C:13]([OH:12])[CH:14]=[C:15]([F:31])[CH:16]=2)=[CH:22][CH:23]=1)(=[O:30])[CH3:29]

参加物

5

反応物 3

HCID 887MethanolHCID 25134Boron tribromideHCID 687420264'-Acetoxy-5-benzyloxy-3-fluorostilbene

生成物 1

HCID 687448004'-Acetoxy-3-fluoro-5-hydroxystilbene収率 61.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-20 °C

実験手順

A 1 M solution of BBr3 (9 ml, 9 mmol) in CH2Cl2 was added to a well-stirred solution of 5-benzyloxy-3-fluoro-4′-acetoxystilbene (1.09 g, 3 mmol) in dry CH2Cl2 (120 mL) at −78° C. The mixture was warmed to −20° C. and stirred for 10 minutes. Then MeOH was added at −78° C. The mixture was washed with saturated NaHCO3, and water, dried over Na2SO4, filtered and evaporated. The 4′-acetoxy-3-fluoro-5-hydroxystilbene (0.50 g, 61%) was obtained as white solid. To a solution of the crude 4′-acetoxy-3-fluoro-5-hydroxystilbene (0.50 g, 1.8 mmol) in MeOH (7.5 ml) was added 3.7 ml 4M HCl in 1,4-dioxane. The mixture was stirred for 20 minutes at ambient temperature. After purification by flash column, 3-fluoro-5,4′-dihydroxystilbene (0.33 g, 780%) was obtained. Data are: 1H NMR (Aceton-d6, 300 MHz) δ 8.624 (s, 2H), 7.46 (m, 2H), 7.06 (q, 2H), 6.84 (m, 4H), 6.66 (dt, 1H); 13C NMR (Aceton-d6, 75 MHz) δ 164.90 (d), 159.96 (d), 158.57, 142.02 (d), 130.84, 129.63, 129.10, 125.55 (d), 116.53, 110.28 (d), 104.44 (d), 102.00 (d); 19F NMR (Aceton-d6, 282 MHz) δ-32429.72 (t); HRMS (EI+) found 230.0738, calcd 230.0743 for C14H, FO2.

後処理

  1. washThe mixture was washed with saturated NaHCO3, and water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

出典と根拠

ORDレコード
ord-b367b2385c704fc9b362b5a9acf91251
出典データセット
uspto-grants-2010_05
特許番号
US07714161B2

反応ノート

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