Methanol → Methyl 2-(4-cyano-2,5-difluorophenyl)acetate

HRID 1519528Notes

Reaction equation

HRID 1519528 reaction equation
[C:1]([C:3]1[C:8]([F:9])=[CH:7][C:6]([CH2:10][C:11]([OH:13])=[O:12])=[C:5]([F:14])[CH:4]=1)#[N:2].S(Cl)(Cl)=O.[CH3:19]O>>[CH3:19][O:12][C:11](=[O:13])[CH2:10][C:6]1[CH:7]=[C:8]([F:9])[C:3]([C:1]#[N:2])=[CH:4][C:5]=1[F:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 675133414-Cyano-2,5-difluorophenylacetic acid

Product 1

HCID 86694454Methyl 2-(4-cyano-2,5-difluorophenyl)acetate

Conditions

Temperature
85 °C

Procedure

(4-Cyano-2,5-difluorophenyl)acetic acid (0.5 g, 2.5 mmol) was dissolved in methanol (20 mL), and thionyl chloride (0.5 mL) was added drop wise to the solution. The reaction was heated to 85° C. for 4 hours. Then it was cooled and evaporated to dryness in vacuo. The residue was partitioned between ethyl acetate and saturated NaHCO3. The organic layer was dried over MgSO4, filtered, and the filtrate was evaporated to dryness under reduced pressure to yield the title compound after purification on silica gel (eluted with 5-20% ethyl acetate-hexanes) as an off white solid. 1H NMR (500 MHz, CDCl3): δ 7.31 (dd, J=5.2, J=5.2 Hz, 1H), 7.19 (dd, J=5.7, J=5.8 Hz, 1H), 3.73 (s, 3H), 3.71 (s, 2H). LC-MS (IE, m/z): 212 [M+1]+.

Workup

  1. temperatureThen it was cooled
  2. customevaporated to dryness in vacuo
  3. customThe residue was partitioned between ethyl acetate and saturated NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-0058fd27978b4e5eaf30f9c75f5535a5
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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