Trifluoroacetic acid → 4-Cyano-2,5-difluorophenylacetic acid

HRID 1519527Notes

Reaction equation

HRID 1519527 reaction equation
C([O:5][C:6](=[O:25])[CH:7]([C:15]1[CH:20]=[C:19]([F:21])[C:18]([C:22]#[N:23])=[CH:17][C:16]=1[F:24])C(OC(C)(C)C)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:22]([C:18]1[C:19]([F:21])=[CH:20][C:15]([CH2:7][C:6]([OH:25])=[O:5])=[C:16]([F:24])[CH:17]=1)#[N:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86694453Di-tert-butyl (4-cyano-2,5-difluorophenyl)propanedioate

Product 1

HCID 675133414-Cyano-2,5-difluorophenylacetic acidYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the di-tert-butyl(4-cyano-2,5-difluorophenyl)propanedioate (10.0 g, 28.3 mmol) in dichloromethane (30 mL) was added triflouroacetic acid (10 mL) and the 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 (5 g, 90%, 85% purity as indicated by NMR). The residue was used in the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 7.31 (dd, J=3, J=2 Hz, 1H), 7.21 (dd, J=5.8, J=5.8 Hz, 1H), 3.67 (s, 2H). LC-MS (IE, m/z): 198 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-08b75ccf92d84491b19f4bab523eab31
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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