Water → HCID 22481230, compound

HRID 2181591Notes

Reaction equation

HRID 2181591 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12].[S:13]1[C:17](B(O)O)=[CH:16][C:15]2[CH:21]=[CH:22][CH:23]=[CH:24][C:14]1=2.C(OCC)(=O)C.O>C1(C)C=CC=CC=1.C(O)C.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>[N+:9]([C:5]1[C:6]([CH3:8])=[CH:7][C:2]([C:17]2[S:13][C:14]3[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=3[CH:16]=2)=[C:3]([CH3:12])[CH:4]=1)([O-:11])=[O:10]

Participants

8

Reactant 4

HCID 962WaterHCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 8857Ethyl AcetateHCID 8258081-Bromo-2,5-dimethyl-4-nitrobenzene

Product 1

HCID 22481230HCID 22481230, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2-bromo-5-nitro-p-xylene (200 g), 2-benzo[b]thiopheneboronic acid (200 g), (Ph3P)4Pd (0.36 g) in toluene (60 ml) and ethanol (22 ml) was heated to reflux overnight. Ethyl acetate and water were added and the organic phase was separated. The organic phase was washed with water, dried (MgSO4) and filtered through a pad of silica to give the title product.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customthe organic phase was separated
  4. washThe organic phase was washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered through a pad of silica

Sources & evidence

ORD record
ord-b3ea34a2a49448b1868cb32b9b2f5b0b
Source dataset
uspto-grants-2005_05
Patent number
US06893650B1

Reaction notes

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