Trifluoroacetic acid → 2-(3-Bromo-4-cyanophenyl)acetic acid

HRID 1519531Notes

Reaction equation

HRID 1519531 reaction equation
C([O:5][C:6](=[O:24])[CH:7]([C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[C:17]([Br:23])[CH:16]=1)C(OC(C)(C)C)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Br:23][C:17]1[CH:16]=[C:15]([CH2:7][C:6]([OH:24])=[O:5])[CH:20]=[CH:19][C:18]=1[C:21]#[N:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67517893di-tert-Butyl (3-bromo-4-cyanophenyl)malonate

Product 1

HCID 665249442-(3-Bromo-4-cyanophenyl)acetic acidYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the di-tert-butyl(3-bromo-4-cyanophenyl)malonate (2.2 g, 5.4 mmol) in dichloromethane (30 mL) was added triflouroacetic acid (10 mL) and the reaction mixture stirred for 12 h at room temperature. The solution was concentrated under reduced pressure and chased with toluene (2×) to give the crude product as a yellowish oil (1 g, 77%, and 85% purity as indicated by NMR). The residue was used in the next step without further purification. 1H NMR (500 MHz, DMSO-d6) δ 12.80 (br s, 1H), 7.87 (d, J=8 Hz, 1H), 7.80 (s, 1H), 7.48 (d, J=8 Hz, 1H), 3.73 (s, 2H). LC-MS (IE, m/z): 240 [M+1]+.

Workup

  1. concentrationThe solution was concentrated under reduced pressure and chased with toluene (2×)

Sources & evidence

ORD record
ord-4b6c1fa9f48f4a90b3600e5a33e43854
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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