Methanol → Methyl (3-bromo-4-cyanophenyl)acetate

HRID 1519532Notes

Reaction equation

HRID 1519532 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].S(Cl)(Cl)=O.[CH3:18]O>>[CH3:18][O:12][C:11](=[O:13])[CH2:10][C:4]1[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 665249442-(3-Bromo-4-cyanophenyl)acetic acid

Product 1

HCID 77231317Methyl (3-bromo-4-cyanophenyl)acetate

Conditions

Temperature
85 °C

Procedure

(3-Bromo-4-cyanophenyl)acetic acid (1.0 g, 4.2 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 h. Then it was cooled to room temperature and evaporated to dryness in vacuo. The residue was partitioned between ethyl acetate and sat. NaHCO3. The organic layer was dried over MgSO4, filtered, and the filtrate was evaporated to dryness under reduced pressure to yield the crude title compound as an off white solid. 1H NMR (500 MHz, CDCl3): δ 7.07 (d, J=7.07 Hz, 1H), 7.00-6.97 (m, 2H), 3.74 (s, 3H), 3.73 (s, 2H). LC-MS (IE, m/z): 195.2 [(M+1)−CO2CH3]+.

Workup

  1. temperatureThen it was cooled to room temperature
  2. customevaporated to dryness in vacuo
  3. customThe residue was partitioned between ethyl acetate and sat. 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-5c72134b906848aeadccc370e4264cb1
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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