Hydrochloric Acid → 5-Bromo-2-formylbenzoic acid

HRID 2278287Notes

Reaction equation

HRID 2278287 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:12]=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Li+].O1CCCC1.Cl>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:12]=[O:13])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 53419722Methyl 5-bromo-2-formylbenzoate

Product 1

HCID 6038605-Bromo-2-formylbenzoic acidYield 74.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 50 mL round-bottom flask was charged with methyl 5-bromo-2-formylbenzoate (1.00 g, 4.11 mmol, 1.00 equiv), lithium hydroxide (2.00 g, 83.5 mmol, 20.0 equiv), tetrahydrofuran (10 mL), and H2O (10 mL). The resulting solution was stirred for 3 h at room temperature. The pH value of the solution was adjusted to 6 with hydrogen chloride solution (2 mol/L). The solid were collected by filtration to yield 0.700 g (crude) of 5-bromo-2-formylbenzoic acid as a light yellow solid. LCMS (ESI, m/z): 227 [M−H]−.

Workup

  1. filtrationThe solid were collected by filtration

Sources & evidence

ORD record
ord-80f360a3fb39420d9a5df1cadabe73bf
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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