Sodium Carbonate → HCID 19430383, compound

HRID 1157145Notes

Reaction equation

HRID 1157145 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]=[O:8])=[C:4]([CH3:9])[CH:3]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=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>[CH3:9][C:4]1[CH:3]=[C:2]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:6][C:5]=1[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 151154075-Bromo-3-methylthiophene-2-carbaldehyde

Product 1

HCID 19430383HCID 19430383, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 5-bromo-3-methyl-thiophene-2-carbaldehyde (1.00 g, 4.88 mmol) in ethylene glycol dimethyl ether (9 ml) was added phenylboronic acid (0.773 g, 6.34 mmol), 2M Na2CO3 solution (6.3 ml) and Pd(PPh3)4 [0.282 g, 0.24 mmol). The mixture was heated for 18 hours, cooled and the solvent removed at reduced pressure to leave a brown residue which was partitioned between water (15 ml) and dichloromethane (20 ml). The organic was separated, washed with water (2×5 ml), brine (10 ml), dried (MgSO4) and the solvent removed at reduced pressure to give a brown oil. Purification by flash column chromatography (6:1 petrol 40-60° C./ethyl acetate) gave the sub-title compound as a yellow oil (0.90 g, 91% yield): 1H NMR (400 MHz, CDCl3) δH 2.75 (3H, s), 7.25 (1H, s) 7.35-7.75 (5H, s), 10.05 (1H, s).

Workup

  1. temperatureThe mixture was heated for 18 hours
  2. temperaturecooled
  3. customthe solvent removed at reduced pressure
  4. customto leave a brown residue which
  5. customwas partitioned between water (15 ml) and dichloromethane (20 ml)
  6. customThe organic was separated
  7. washwashed with water (2×5 ml), brine (10 ml)
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed at reduced pressure
  10. customto give a brown oil
  11. customPurification by flash column chromatography (6:1 petrol 40-60° C./ethyl acetate)

Sources & evidence

ORD record
ord-dc45654bd0174d179b71bfbad5facbc0
Source dataset
uspto-grants-2010_10
Patent number
US07807659B2

Reaction notes

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