Sodium Carbonate → 2-(5-Chloro-2-thienyl)benzaldehyde

HRID 1433066Notes

Reaction equation

HRID 1433066 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].Br[C:13]1[S:14][C:15]([Cl:18])=[CH:16][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:18][C:15]1[S:14][C:13]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH:1]=[O:2])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 761332-Bromo-5-chlorothiopheneHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 183576862-(5-Chloro-2-thienyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Formylphenylboronic acid (1.37 g, 9.15 mmol), 2-bromo-5-chlorothiophene (1 mL, 9.15 mmol), 2M Na2CO3 (9 mL, 18.3 mmol) and Pd(PPh3)4 (0.53 mg, 0.46 mmol) in DME (30 mL) are heated to reflux for 4 h after which time the reaction mixture is concentrated in vacuo and taken up in EtOAc. The organic solution is washed with water (×2) then brine and dried over MgSO4, filtered and concentrated to dryness. The crude residue is purified by chromatography using 5% EtOAc/hexanes as the eluent to yield a yellow solid (1.8 g, 8.1 mmol) as the title compound. EI MS [M]+=222, 224, Cl pattern.

Workup

  1. temperatureto reflux for 4 h after which time the reaction mixture
  2. concentrationis concentrated in vacuo
  3. washThe organic solution is washed with water (×2)
  4. dry with materialbrine and dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude residue is purified by chromatography

Sources & evidence

ORD record
ord-9b700b136f5240fb9db225ab6e621d92
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

Loading…