Methyl 4-bromobenzoate → Methyl 4-(thiophen-2-yl)benzoate

HRID 2270741Notes

Reaction equation

HRID 2270741 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.[CH3:9][O:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=1>>[CH3:9][O:10][C:11]([C:12]1[CH:17]=[CH:16][C:15]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[CH:14][CH:13]=1)=[O:19]

Participants

3

Reactant 2

HCID 12081Methyl 4-bromobenzoateHCID 27339602-Thiopheneboronic acid

Product 1

HCID 3697617Methyl 4-(thiophen-2-yl)benzoateYield 65%

Procedure

2-(4-methoxycarbonylphenyl)thiophene was prepared in the same manner as described in Example 32C from thiophene-2-boronic acid (1.0 g, 7.81 mmol) and methyl-4-bromobenzoate (1.68 g, 7.81 mmol). Purification by column chromatography using 2% ethyl acetate/hexanes gave 1.1 g of 2-(4-methoxycarbonylphenyl)thiophene as a white solid (65% yield).

Workup

  1. custom2-(4-methoxycarbonylphenyl)thiophene was prepared in the same manner
  2. customPurification by column chromatography

Sources & evidence

ORD record
ord-9d0d32b93b354c30bedc812d9c821b32
Source dataset
uspto-grants-2001_12
Patent number
US06331637B1

Reaction notes

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