Sulfuric Acid → Tert-butyl 4-(bromomethyl)benzoate

HRID 1771038Notes

Reaction equation

HRID 1771038 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[C:12](O)([CH3:15])([CH3:14])[CH3:13].[O-]S([O-])(=O)=O.[Mg+2].S(=O)(=O)(O)O>ClCCl>[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 225994-(Bromomethyl)benzoic acidHCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 11414578Tert-butyl 4-(bromomethyl)benzoateYield 39.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared from 4-(bromomethyl)benzoic acid (2.15 g; 10.0 mmol), t-butyl alcohol (4.8 mL; 50 mmol), anhydrous MgSO4 (4.8 g; 40 mmol), and concentrated sulphuric acid in dichloromethane (40 mL) as described in Example 6a. After 14 days, the mixture was worked up as described in Example 6a. 1.07 g (39%) product was obtained (white solid). The product was used in 7b without further purification.

Sources & evidence

ORD record
ord-5990551fc5764802b5b68e390248c119
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

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