Sulfuric Acid → 4-Bromo-2,6-diethylbenzoic acid

Reaction equation

[Br:1][C:2]1[CH:20]=[C:19]([CH2:21][CH3:22])[C:5]([C:6](NC2C=CC=C3C=2N=CC=C3)=[O:7])=[C:4]([CH2:23][CH3:24])[CH:3]=1.S(=O)(=O)(O)[OH:26]>>[Br:1][C:2]1[CH:3]=[C:4]([CH2:23][CH3:24])[C:5]([C:6]([OH:7])=[O:26])=[C:19]([CH2:21][CH3:22])[CH:20]=1

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 86699768HCID 86699768, compound

Product 1

HCID 532567664-Bromo-2,6-diethylbenzoic acidYield 56%

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-bromo-2,6-diethyl-N-quinolin-8-yl-benzamide (2.9 g, 7.6 mmol) in 40% sulphuric acid (15 ml) is heated at 120° C. for 16 h. After completion, the reaction mixture is extracted with ether (2×100 ml) and the combined organic layers are dried over sodium sulfate and concentrated to obtain 4-bromo-2,6-diethyl-benzoic acid (1.1 g, 4.28 mmol, 56%).

Workup

extractionAfter completion, the reaction mixture is extracted with ether (2×100 ml)
dry with materialthe combined organic layers are dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-918def4a46ee460c8546069c4ceae6d3
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108936B2

Reaction notes

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