5-Bromo-2-iodotoluene → 5-(3-Cyano-4-fluorophenyl)-2-(4-bromo-2-methylphenyl)thiophene

HRID 1821048Notes

Reaction equation

HRID 1821048 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([CH3:9])[CH:3]=1.[Br-].[C:11]([C:13]1[CH:14]=[C:15]([Zn+])[CH:16]=[CH:17][C:18]=1[F:19])#[N:12].[Br-].[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[Zn+]>>[C:11]([C:13]1[CH:14]=[C:15]([C:23]2[S:22][C:26]([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=3[CH3:9])=[CH:25][CH:24]=2)[CH:16]=[CH:17][C:18]=1[F:19])#[N:12]

Participants

4

Reactant 3

HCID 27246015-Bromo-2-iodotolueneHCID 178419761HCID 178419761, compoundHCID 178510271HCID 178510271, compound

Product 1

HCID 688529615-(3-Cyano-4-fluorophenyl)-2-(4-bromo-2-methylphenyl)thiophene

Procedure

The title compound was prepared using a procedure analogous to that described in EXAMPLE 127, Step A substituting 5-bromo-2-(4-bromo-2-methylphenyl)thiophene (from Step B) for 4-bromo-2-methyliodobenzene and 3-cyano-4-fluorophenylzincbromide for 2-thienylzinc bromide: 1H NMR (CDCl3) 7.85 (m, 2H), 7.47 (d, J=2.0, 1H), 7.40 (dd, J=2.0, 9.0, 1H), 7.29 (m, 3H), 7.07 (d, J=6.5, 1H), 2.47 (s, 3H). HPLC A 4.20 min.

Workup

  1. customA 4.20 min.

Sources & evidence

ORD record
ord-1b7f5b158ea04322bcaa45efed21b5e2
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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