5-Bromo-2-iodotoluene → 2-(4-Bromo-2-methylphenyl)thiophene

HRID 1821046Notes

Reaction equation

HRID 1821046 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([CH3:9])[CH:3]=1.[Br-].[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[Zn+]>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.C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[S:11][CH:15]=[CH:14][CH:13]=2)=[C:4]([CH3:9])[CH:3]=1

Participants

5

Reactant 2

HCID 27246015-Bromo-2-iodotolueneHCID 178419761HCID 178419761, compound

Product 1

HCID 688515822-(4-Bromo-2-methylphenyl)thiophene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Bromo-2-methyliodobenzene (1.0 mmol) was combined with THF solution of 2-thienylzinc bromide (2.0 mmol) in an oven-dried tube under argon. The resulting solution was degassed with a steady stream of argon for 10 min at rt. To this mixture, solid (Ph3P)4Pd (0.1 mmol) was added and the mixture was degassed with argon for 2 min after which it was stirred at rt for 8 h. The reaction mixture was combined with 1M HCl (100 mL) and ethyl acetate (200 mL). Organic layer was separated, washed sequentially with 1M hydrochloric acid (50 mL) and brine (50 mL), and dried over sodium sulfate. The desired product was isolated by flash chromatography on silica gel using hexanes as the eluant: 1H NMR (CDCl3) 7.45 (d, J=1.0, 1H), 7.39 (d, J=5.6, 1H), 7.37 (dd, J=1.0, 5.0, 1H), 7.28 (d, J=5.0, 1H), 7.13 (m, 1H), 7.08 (d, J=5.6, 1H); HPLC A 4.09 min; ESI-MS (m/z)=252, 254.

Workup

  1. customThe resulting solution was degassed with a steady stream of argon for 10 min at rt
  2. customthe mixture was degassed with argon for 2 min after which it
  3. customOrganic layer was separated
  4. washwashed sequentially with 1M hydrochloric acid (50 mL) and brine (50 mL)
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-acfff433501f4ac0a9c5a246ef852dd2
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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