Ethyl 4-iodobenzoate → 1152-30-3

HRID 533715Notes

Reaction equation

HRID 533715 reaction equation
I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH:13](/B(O)O)=[CH:14]\[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[CH:13](/[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1)=[CH:14]\[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 142891Ethyl 4-iodobenzoateHCID 5702628Styrylboronic acid

Product 1

HCID 59079071152-30-3Yield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of ethyl 4-iodobenzoate (1.0 g, 3.6 mmol) in DMF (4 mL) was added commercial (E)-styrylboronic acid (538 mg, 3.6 mmol) and catalytic Pd(tBuP)2. The reaction vessel was sealed and heated at 160° C. for 10 minutes in a microwave reactor. The reaction was cooled to rt, diluted with EtOAc:hexanes (2:1, 20 mL) and washed with water (2×20 mL) and brine (20 mL). The organic phase was dried over MgSO4, filtered and concentrated under vacuum. The crude product was purified by column chromatography (silica gel) using 0 to 10% EtOAc/hexanes to afford (E)-ethyl 4-styrylbenzoate (771 mg, 85%) as a pale yellow solid; 1H-nmr (400 MHz, CDCl3) δ 8.05 (d, J=8.0 Hz, 2H), 7.61 (d, J=8.0 Hz, 2H), 7.56 (dd, J=8.0, 2.0 Hz, 2H), 7.41-7.37 (m, 3H), 6.95 (d, 1H), 6.89 (d, 1H), 4.41 (q, J=7.0 Hz, 2H), 1.44 (t, J=6.8 Hz, 3H); LCMS (214 nM) 3.58 min (>98%); MS (ESI) m/z=253.1.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction was cooled to rt
  3. washwashed with water (2×20 mL) and brine (20 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-1d808382e8eb4434bdad84625400cc12
Source dataset
uspto-grants-2014_10
Patent number
US08853392B2

Reaction notes

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