반응 #74683

반응 방정식

triethylamine

potassium acetate

3-furylboronic acid

2-Iodo-4-(trifluoromethyl)phenol

acetic anhydride

→

title product

수율 86.6%

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

수율 86.6%

용매

tert-butyl methyl ether

2-methyl tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타the reaction degassed 3 more times
3. 3
   온도The reaction was then cooled
4. 4
   기타partitioned between EtOAc (50 mL) and water (50 mL)
5. 5
   기타the organic layer was separated
6. 6
   기타dried in vacuo
7. 7
   기타to give a brown oil
8. 8
   기타The reaction was then partitioned between EtOAc (30 ml) and water (30 ml)
9. 9
   기타organic layer was dried in vacuo
10. 10
    기타to give a brown oil which
11. 11
    기타crystallised
12. 12
    기타This was triturated with heptane

실험 절차

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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