反応 #74683

反応方程式

triethylamine

potassium acetate

3-furylboronic acid

2-Iodo-4-(trifluoromethyl)phenol

acetic anhydride

→

title product

収率 86.6%

2-(3-Furyl)-4-(trifluoromethyl)phenyl acetate

収率 86.6%

溶媒

tert-butyl methyl ether

2-methyl tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他the reaction degassed 3 more times
3. 3
   温度The reaction was then cooled
4. 4
   その他partitioned between EtOAc (50 mL) and water (50 mL)
5. 5
   その他the organic layer was separated
6. 6
   その他dried in vacuo
7. 7
   その他to give a brown oil
8. 8
   その他The reaction was then partitioned between EtOAc (30 ml) and water (30 ml)
9. 9
   その他organic layer was dried in vacuo
10. 10
    その他to give a brown oil which
11. 11
    その他crystallised
12. 12
    その他This was triturated with heptane

実験手順

2-Iodo-4-(trifluoromethyl)phenol (9.9 g, 0.0344 mol) was dissolved in 2-methyl tetrahydrofuran (100 mL) then potassium acetate (11.8 g, 0.12 mol) and 3-furylboronic acid (5.0 g, 0.0447 mol) was added and the reaction degasses 3 times before bis(tri-tert-butylphosphine) palladium (0) (1.0 g, 0.00196 mol) was added and the reaction degassed 3 more times. The reaction was then stirred at 90° C. under nitrogen for 18 hours. The reaction was then cooled and partitioned between EtOAc (50 mL) and water (50 mL), the organic layer was separated and dried in vacuo to give a brown oil. This was dissolved in tert-butyl methyl ether (50 mL), triethylamine (7.2 mL, 0.051 mol) added then acetic anhydride (4.7 mL, 0.051 mol) and stirred for 2 hours at room temperature. The reaction was then partitioned between EtOAc (30 ml) and water (30 ml) then organic layer was dried in vacuo to give a brown oil which crystallised upon standing. This was triturated with heptane to give the title product as a pale brown solid (8.04 g, 86.6%). LCMS Rt=1.70 min. 1H NMR (400 MHz, CDCl3): δ 2.34 (s, 3H), 6.67 (s, 1H) 7.26 (m, 1H) 7.51 (s, 1H), 7.57 (d, 1H), 7.76 (m 2H)

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