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Pivalic acid → 2-(4-Fluoro-2-methylphenyl)-6-methoxybenzo[b]thiophene

HRID 632620
Notes
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Reaction equation

HRID 632620 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[CH:9][S:8][C:7]=2[CH:11]=1.Br[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[CH3:20].CC(C)(C)C(O)=O.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O.C(Cl)Cl.O.CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=C(OC)C=CC=2OC)=C(C(C)C)C=1)C.C1C=[C-]C(CCN)=CC=1.Cl[Pd+]>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:9]2[S:8][C:7]3[CH:11]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=3[CH:10]=2)=[C:14]([CH3:20])[CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 6417Pivalic acidHCID 11430Potassium CarbonateHCID 967432-Bromo-5-fluorotolueneHCID 136342376-Methoxy-1-benzothiophene

Product 1

HCID 867306312-(4-Fluoro-2-methylphenyl)-6-methoxybenzo[b]thiopheneYield 44%

Reagents, catalysts & solvents 4

HCID 25112666
BrettPhos Palladacycle
Catalyst
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent
HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

To a 20 mL microwave vial, 6-methoxybenzo[b]thiophene (1 g, 6.09 mmol), 2-bromo-5-fluorotoluene (0.808 mL, 6.39 mmol), BrettPhos palladacycle(1 st generation) (0.243 g, 0.304 mmol), trimethylacetic acid (1.866 g, 18.27 mmol), and K2CO3 (2.52 g, 18.27 mmol) were suspended in DMA (10 mL). The reaction was heated for 90 min at 150° C. under microwave radiation. The reaction mixture was diluted with DCM and water. The organic layer was collected (phase separator) and concentrated to afford the crude product. The crude material was concentrated onto to silica gel and purified by column chromatography (SiO2, 100% Heptanes) to afford 2-(4-fluoro-2-methylphenyl)-6-methoxybenzo[b]thiophene (730 mg, 2.68 mmol, 44% yield) as a white solid. 1H NMR (400 MHz, CDCL3) δ ppm=7.69 (d, J=9.09 Hz, 1H), 7.43 (dd, J=6.06, 8.59 Hz, 1H), 7.35 (d, J=2.53 Hz, 1H), 7.14 (s, 1H), 7.00-7.10 (m, 2H), 6.90-7.00 (m, 1H), 3.92 (s, 3H), 2.47 (s, 3H).

Workup

  1. customThe organic layer was collected (phase separator)
  2. concentrationconcentrated
  3. customto afford the crude product
  4. concentrationThe crude material was concentrated onto to silica gel
  5. custompurified by column chromatography (SiO2, 100% Heptanes)

Sources & evidence

ORD record
ord-42bb359e793e4161a0c6f6b750ad87a5
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321746B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes