4-Bromo-2-furaldehyde → HCID 59648529, compound

HRID 2105560Notes

Reaction equation

HRID 2105560 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[O:5][CH:6]=1.[C:9]1(/[CH:15]=[CH:16]/B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(C1OC(C=O)=CC=1)C1C=CC=CC=1>CN(C=O)C>[CH:16](/[C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[O:5][CH:6]=1)=[CH:15]\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 27570104-Bromo-2-furaldehydeHCID 5702628Styrylboronic acidHCID 124185375-Benzylfuran-2-carbaldehyde

Product 1

HCID 59648529HCID 59648529, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized from 4-bromo-furan-2-carboxaldehyde (1.1 g, 6.3 mmol, 1 equiv) and trans-phenylvinyl-boronic acid (1.4 g, 9.4 mmol, 1.5 equiv) using the conditions used to synthesize 5-benzyl-furan-2-carbaldehyde, with the exception that the reaction was run in DMF (25 mL). The resulting residue was purified via ISCO Companion (0-30% EtOAc/heptane) and preparative HPLC using the Chromeleon purification system (0.1% formic acid/1% acetonitrile mixture in water (aqueous phase) and methanol (no modifier added—organic phase) using a 50 mm Dynamax HPLC C-18 column at 28 mL/min (initial gradient of 40% methanol and increasing to 100% over 7 min)) afforded a clean product, retention time of product: 3.4-3.6 min. Amount of (E)-4-styrylfuran-2-carbaldehyde isolated: 89.1 mg (7% yield). 1H NMR (400 MHz, CD3CN) δ (ppm): 9.62 (d, J=0.59 Hz, 1 H), 7.91 (s, 1 H), 7.63 (d, J=0.63 Hz, 1 H), 7.50-7.55 (m, 2 H), 7.35-7.42 (m, 2 H), 7.26-7.32 (m, 1 H), 7.08 (s, 2 H).

Workup

  1. customThe resulting residue was purified via ISCO Companion (0-30% EtOAc/heptane) and preparative HPLC
  2. customthe Chromeleon purification system (0.1% formic acid/1% acetonitrile mixture in water (aqueous phase) and methanol (no modifier added—organic phase)
  3. temperatureincreasing to 100% over 7 min))
  4. customafforded a clean product, retention time of product
  5. custom3.4-3.6 min

Sources & evidence

ORD record
ord-b958e076a3034043a13d8460fbdc4fe2
Source dataset
uspto-grants-2009_08
Patent number
US07579370B2

Reaction notes

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