Reaction #74683

Reaction equation

triethylamine

potassium acetate

3-furylboronic acid

2-Iodo-4-(trifluoromethyl)phenol

acetic anhydride

→

title product

Yield 86.6%

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

Yield 86.6%

Solvents

tert-butyl methyl ether

2-methyl tetrahydrofuran

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Otherthe reaction degassed 3 more times
3. 3
   TemperatureThe reaction was then cooled
4. 4
   Otherpartitioned between EtOAc (50 mL) and water (50 mL)
5. 5
   Otherthe organic layer was separated
6. 6
   Otherdried in vacuo
7. 7
   Otherto give a brown oil
8. 8
   OtherThe reaction was then partitioned between EtOAc (30 ml) and water (30 ml)
9. 9
   Otherorganic layer was dried in vacuo
10. 10
    Otherto give a brown oil which
11. 11
    Othercrystallised
12. 12
    OtherThis was triturated with heptane

Procedure

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)

Source