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Water → 2-Acetyl-4-(2-n-butoxy-3,5-di-iso-propylphenyl)-5-fluorobenzo[b]thiophene

HRID 1394607
Notes
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Reaction equation

HRID 1394607 reaction equation
[CH:1]([C:4]1[C:5]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[C:6](B(O)O)[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2].[C:21]([C:24]1[S:28][C:27]2[CH:29]=[CH:30][C:31]([F:34])=[C:32](I)[C:26]=2[CH:25]=1)(=[O:23])[CH3:22].C(=O)([O-])[O-].[Na+].[Na+].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>[C:21]([C:24]1[S:28][C:27]2[CH:29]=[CH:30][C:31]([F:34])=[C:32]([C:6]3[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=[C:4]([CH:1]([CH3:2])[CH3:3])[C:5]=3[O:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:26]=2[CH:25]=1)(=[O:23])[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 17952696(2-Butoxy-3,5-diisopropylphenyl)-boronic acidHCID 179527762-Acetyl-4-iodo-5-fluorobenzo[b]thiophene

Product 1

HCID 179527492-Acetyl-4-(2-n-butoxy-3,5-di-iso-propylphenyl)-5-fluorobenzo[b]thiophene

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 702EthanolSolvent
HCID 1140TolueneSolvent

Procedure

A mixture of 1.08 mmol of 3,5-di-iso-propyl-2-n-butoxy phenylboronic acid, 1.62 mmol of 2-acetyl-4-iodo-5-fluorobenzo[b]thiophene and 62 mg (0.05 mmol) of Pd(PPh3)4, 1 mL of 2N aqueous sodium carbonate in 9 mL of toluene and 4 mL ethanol was heated to reflux. After complexion (TLC), water was added and the solution was extracted with ethyl acetate. The organic layer is dried over MgSO4 and after evaporation of the solvents, the crude oil was purified over a short silica plug (eluent: 10/90=ethyl acetate/hexane) to afford 2-acetyl-4-(2-n-butoxy-3,5-di-iso-propylphenyl)-5-fluorobenzo[b]thiophene.

Workup

  1. temperaturewas heated to reflux
  2. extractionthe solution was extracted with ethyl acetate
  3. dry with materialThe organic layer is dried over MgSO4
  4. customafter evaporation of the solvents
  5. customthe crude oil was purified over a short silica plug (eluent: 10/90=ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ca5612ba35774f0fbd51e8bffda2990c
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07348359B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes