Triethylamine → 3-Bromo-2-fluorobenzamide

HRID 1879049Notes

Reaction equation

HRID 1879049 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].C([N:14](CC)CC)C.S(Cl)(Cl)=O>O1CCCC1>[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:14])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 27363133-Bromo-2-fluorobenzoic acid

Product 1

HCID 442031023-Bromo-2-fluorobenzamideYield 46.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-2-fluorobenzoic acid (3.77 g, 17.2 mmol) in dry tetrahydrofuran (200 ml) was added triethylamine (4.77 ml, 34.4 mmol) and thionyl chloride (1.69 ml, 21.5 mmol). The reaction mixture was stirred for 1 h and then quenched with ammonia in methanol (10 ml, saturated). After an additional hour of stirring the mixture was evaporated and the crude product was purified by flash column chromatography (ethyl acetate/isooctane 1:1) to give the title compound (1.76 g). MS m/z (rel. intensity, 70 eV) 219 (M+, 26), 217 (M+, 26), 203 (62), 201 (70), 94 (bp).

Workup

  1. customquenched with ammonia in methanol (10 ml, saturated)
  2. stirringAfter an additional hour of stirring the mixture
  3. customwas evaporated
  4. customthe crude product was purified by flash column chromatography (ethyl acetate/isooctane 1:1)

Sources & evidence

ORD record
ord-6e1cac2fdc4a46408609b511fc19f0b7
Source dataset
uspto-grants-2012_11
Patent number
US08314126B2

Reaction notes

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