3-Bromothiophene → 3-Hexylthiophene

HRID 1775785Notes

Reaction equation

HRID 1775785 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Br[C:10]1[CH:14]=[CH:13][S:12][CH:11]=1>>[CH2:1]([C:10]1[CH:14]=[CH:13][S:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 133833-BromothiopheneHCID 178444609HCID 178444609, compound

Product 1

HCID 5668493-Hexylthiophene

Procedure

In the presence of 0.0012 eq. of [1,3-bis(diphenylphosphine)propane]dichloronickel (II) (Ni(dppp)Cl2) catalyst, 1.3 eq. of hexylmagnesium bromide (Hexyl-MgBr) is added to 3-bromothiophene monomer to obtain 3-hexylthiophene, and then 2 eq. of N-bromosuccimide (NBS) is further added thereto to obtain 2,5-dibromo-3-hexylthiophene monomer.

Sources & evidence

ORD record
ord-5c33268f39f54d1dbb78f9fb27499bba
Source dataset
uspto-grants-2016_02
Patent number
US09260572B2

Reaction notes

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