Sodium Hydroxide → 2-Bromo-5-(4-bromo-2-methylphenyl)thiophene

HRID 1821047Notes

Reaction equation

HRID 1821047 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[C:4]([CH3:13])[CH:3]=1.C([O-])(=O)C.[Na+].[Br:19]Br.[OH-].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Br:19][C:10]1[S:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[CH3:13])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 517045Sodium AcetateHCID 688515822-(4-Bromo-2-methylphenyl)thiophene

Product 1

HCID 688529502-Bromo-5-(4-bromo-2-methylphenyl)thiophene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred homogeneous solution of 2-(4-bromo-2-methylphenyl)thiophene (5.0 mmol, from Step A) and sodium acetate (10 mmol) in acetic acid (25 mL), bromine (5.0 mmol) was added dropwise via syringe at rt over 20-30 min and the resulting mixture was stirred for 1 h. The reaction mixture was combined with 1 M sodium hydroxide (250 mL) and ethyl acetate (250 mL). Organic layer was separated, washed sequentially with 1M sodium hydroxide (100 mL) and brine (100 mL), and dried over sodium sulfate. Silica gel chromatography using hexanes as the eluant afforded the title compound: 1H NMR (CDCl3) 7.46 (d, J=0.6, 1H), 7.38 (dd, J=3.9, 0.6, 1H), 7.24 (d, J=3.9, 1H), 7.09 (d, J=2.9, 1H), 6.83 (d, J=2.9, 1H), 2.43 (s, 3H); HPLC A 4.41 min, ESI-MS (m/z)=334.

Workup

  1. customOrganic layer was separated
  2. washwashed sequentially with 1M sodium hydroxide (100 mL) and brine (100 mL)
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-795bc5f9ba1346d7aa30e81aae0cc1c3
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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