Sulfuric Acid → 2-Bromomethylphenylacetic acid t-butyl ester

HRID 397475Notes

Reaction equation

[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=[O:11].S(=O)(=O)(O)O.[CH3:18][C:19](=[CH2:21])[CH3:20].C(=O)(O)[O-].[Na+]>O1CCOCC1.COC(C)(C)C>[C:19]([O:11][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][Br:1])([CH3:21])([CH3:20])[CH3:18]

Participants

Conditions

Temperature: -15 °C

Procedure

To a solution of 80 g (0.349 mol) 2-bromomethylphenylacetic acid in 700 mL 1,4-dioxane in a 2 L heavy-walled flask was added 84 mL (1.571 mol) concentrated sulfuric acid at ambient temperature. The reaction mixture was chilled to −15° C., and 580 mL isobutylene was condensed directly into the reaction vessel. The sealed pressure flask was shaken mechanically at room temperature for 4 h (the pressure inside the flask rises to ca. 20 psi during this step). The mixture was carefully quenched by slowly pouring it into a 0-5° C. stirred mixture of 1.2 L tert-butyl methyl ether and 336 g (4.0 mol) solid sodium bicarbonate before slow dilution with 1.2 L ice-water. The separated organic phase was washed with 0.8 L brine, dried with sodium sulfate, filtered concentrated in vacuo to give an oil, which was used without further purification.

Workup

customcondensed directly into the reaction vessel
customThe mixture was carefully quenched
additionby slowly pouring it into a 0-5° C.
stirringstirred
washThe separated organic phase was washed with 0.8 L brine
dry with materialdried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customto give an oil, which
customwas used without further purification

Sources & evidence

ORD record: ord-7e5bab0db56749dea4088df587c46272
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610701B2

Reaction notes

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