Ethanol → Ethyl 4-(bromomethyl)-3-(trifluoromethyl)benzoate

HRID 1184846Notes

Reaction equation

[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].OS(O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+].[CH2:27](O)[CH3:28]>>[CH2:27]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([CH2:2][Br:1])=[C:4]([C:12]([F:13])([F:14])[F:15])[CH:5]=1)[CH3:28]

Participants

Reactant 4

HCID 702Ethanol

HCID 1118Sulfuric Acid

HCID 10340Sodium Carbonate

HCID 231458934-(Bromomethyl)-3-(trifluoromethyl)benzoic acid

Product 1

HCID 23073576Ethyl 4-(bromomethyl)-3-(trifluoromethyl)benzoateYield 77%

Conditions

Temperature: 80 °C

Procedure

4-(bromomethyl)-3-(trifluoromethyl)benzoic acid 35 (650 mg, 2.296 mmol) was dissolved in ethanol (30 mL). Concentrated H2SO4 (1.224 mL, 22.96 mmol) was slowly added. The resulting mixture was heated at 80° C. overnight. The reaction mixture was cooled and neutralized with saturated Na2CO3 Solution. The resulting precipitate was collected to give crude 4-bromomethyl-3-trifluoromethyl-benzoic acid ethyl ester 36 (550 mg, 77%) which was used without further purification. (m/z)=311 an 313 (M+H)+.

Workup

temperatureThe reaction mixture was cooled
customThe resulting precipitate was collected

Sources & evidence

ORD record: ord-d40fdc75c4be4577b970cfcdca904486
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669256B2

Reaction notes

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