1,2-Dimethoxyethane → HCID 82392097, compound

HRID 2177329Notes

Reaction equation

HRID 2177329 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8].COCCOC.[Cl:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.O>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[CH:6]=[CH:5][S:4][C:3]=2[CH:7]=[O:8])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 27970793-Bromothiophene-2-carboxaldehyde

Product 1

HCID 82392097HCID 82392097, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 3-bromothiophene-2-carbaldehyde (10 g, 52.34 mmol, 1.00 equiv), ethylene glycol dimethyl ether (120 mL), (4-chlorophenyl)boronic acid (9 g, 57.55 mmol, 1.10 equiv), Pd(PPh3)4 (3 g, 2.60 mmol, 0.05 equiv), sodium carbonate (16.4 g, 154.73 mmol, 2.96 equiv), water (40 mL). The resulting solution was heated to reflux for 4 h. The resulting solution was extracted with 3×100 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×200 mL of brine. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with PE/EA (30/1). This resulted in 12 g (93%) of 3-(4-chlorophenyl)thiophene-2-carbaldehyde as a light yellow solid.

Workup

  1. customInto a 500-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux for 4 h
  5. extractionThe resulting solution was extracted with 3×100 mL of ethyl acetate
  6. washThe resulting mixture was washed with 3×200 mL of brine
  7. concentrationThe resulting mixture was concentrated under vacuum
  8. customThis resulted in 12 g (93%) of 3-(4-chlorophenyl)thiophene-2-carbaldehyde as a light yellow solid

Sources & evidence

ORD record
ord-0d0e0b02fd034838a35e1bbd2c39e7e1
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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