Diethyl Ether → 4-(3-Chlorobenzyl)thiophene-3-carboxylic acid

HRID 870041Notes

Reaction equation

Br[C:2]1[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)=[CH:5][S:4][CH:3]=1.CC[O:17][CH2:18]C.C1C[O:23]CC1>>[Cl:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH2:7][C:6]1[C:2]([C:18]([OH:17])=[O:23])=[CH:3][S:4][CH:5]=1

Participants

Reactant 3

HCID 3283Diethyl Ether

HCID 8028Tetrahydrofuran

HCID 451405813-Bromo-4-(3-chlorobenzyl)thiophene

Product 1

HCID 451405894-(3-Chlorobenzyl)thiophene-3-carboxylic acid

Procedure

3-Bromo-4-(3-chlorobenzyl)thiophene from Example 3, Step 2 (6.22 g, 21.6 mmol) was reacted under conditions similar to Example 1, Step 6 (Et2O was used as a solvent instead of THF), to afford the desired product as an off-white solid that was used directly without further purification.

Sources & evidence

ORD record: ord-c9bb23e6a2bd450c87babcefdd9727ae
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969394B2

Reaction notes

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