Sodium Carbonate → HCID 21182785, compound

HRID 1387065Notes

Reaction equation

HRID 1387065 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9](B(O)O)[S:8][C:7]=2[CH:14]=1.[C:15]([O:19][C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1)([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[Na+].[Na+].[Al]>C1COCC1.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>[C:15]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:9]2[S:8][C:7]3[CH:14]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=3[CH:10]=2)=[CH:22][CH:21]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27639591-Bromo-4-(tert-butoxy)benzeneHCID 5359268AluminumHCID 10560276(6-Methoxy-1-benzothiophen-2-yl)boronic acid

Product 1

HCID 21182785HCID 21182785, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-methoxybenzo[b]thiophene-2-boronic acid (8.87 g, 42.6 mmol) and 4-tert-butoxybromobenzene (U.S. Pat. No. 540,851; 10.25 g, 44.7 mmol) in 400 mL of THF was treated with Pd(PPh3)4 (1.9 g, 1.64 mmol) and 45 mL of 2 N aqueous Na2CO3. The reaction vessel was covered with aluminum foil to keep out light, and the mixture was heated at reflux overnight. After cooling to ambient temperature, the layers were separated, and the aqueous layer was extracted with EtOAc (3×50 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude residue was purified by PrepLC (SiO2; 5% THF in hexanes) to give 8.8 g (28.2 mmol; 66%) of the title product as a white powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (3×50 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified by PrepLC (SiO2; 5% THF in hexanes)

Sources & evidence

ORD record
ord-fdaa62191bf4428da212708784820c9c
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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