Ethyl bromoacetate → HCID 22050564, compound

HRID 1867153Notes

Reaction equation

HRID 1867153 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.[CH2:10]([O:12][C:13](=[O:16])[CH2:14]Br)[CH3:11].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([CH:7]=1)[O:8][CH2:14][C:13]([O:12][CH2:10][CH3:11])=[O:16]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 27746165-Fluoro-2-methylphenol

Product 1

HCID 22050564HCID 22050564, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-fluoro-2-methylphenol (1.00 g, 7.93 mmol) and ethylbromoacetate (1.59 g, 9.51 mmol) in DMF (15 mL) was added K2CO3 (1.10 g, 7 93 mmol). After 30 min at RT, DMF was removed by distillation. The crude product was washed with 5% citric acid (30 mL) and water (30 mL), extracted in DCM (3×20 mL), dried over Na2SO4, filtered, concentrated, and dried in vacuo. Desired product obtained as yellow oil (1.30 g, 77%). 1H NMR (CD3OD/400 MHz) δ7.09 (t, 1H, J=8.8 Hz), 6.58 (m, 1H), 6.56 (m, 1H), 4.71 (s, 2H), 4.23 (q, 2H, J=7.2 Hz), 2.18 (s, 3H), 1.27 (t, 3H, J=7.2 Hz). ESHRMS m/z 212.0847 (M+H calculated for C11H13FO3 requires 212.0849).

Workup

  1. customDMF was removed by distillation
  2. washThe crude product was washed with 5% citric acid (30 mL) and water (30 mL)
  3. extractionextracted in DCM (3×20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-8a149a18756446a5a1e7e27770bf57ad
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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