Sodium hydride → HCID 69829960, compound

HRID 1386947Notes

Reaction equation

HRID 1386947 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([F:11])[CH:5]=1.[H-].[Na+].Br[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>C(COC)OC>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:6]([F:11])[CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 7019368Methyl 3-fluoro-4-hydroxybenzoate

Product 1

HCID 69829960HCID 69829960, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-fluoro-4-hydroxy-benzoic acid methyl ester (2.5 g, 14.7 mmol), NaH suspension in oil (55%) (641 mg, 14.7 mmol), KI (244 mg, 14.7 mmol, 0.1 eq.) and tert.butyl bromoacetate (3.44 g, 17.6 mmol 1.2 eq.) in dimethoxyethane (20 ml) was heated to 70° C. for 16 hrs. After evaporation of the solvent the residue was chromatographed over 120 g SiO2 (Merck 230-400 mesh) with EtOAc/nHexane 7:93, affording the title compound (3.53 g, 85% yield) as a colorless liquid. MS: m/e=284 (M+).

Workup

  1. customAfter evaporation of the solvent the residue
  2. customwas chromatographed over 120 g SiO2 (Merck 230-400 mesh) with EtOAc/nHexane 7:93

Sources & evidence

ORD record
ord-f66d236a48ee41f3beb916d89ffc1125
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

Loading…