Ethyl bromoacetate → HCID 22050564, compound

HRID 1832110Notes

Reaction equation

HRID 1832110 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>[CH2:10]([O:12][C:13](=[O:16])[CH2:14][O:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[CH3:9])[CH3:11]

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) δ 7.09 (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). ES HRMS m/z 212.0847 (M+H calculated for C11H13FO3 requires 212.0849). Step 2: Preparation of ethyl [2-(bromomethyl)-5-fluorophenoxy]acetate.

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-2d66b3ca0b334c76bbd33ebdec76bdb5
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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