Sodium hydride → HCID 68617899, compound

HRID 1158470Notes

Reaction equation

HRID 1158470 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:12][C:13]([F:16])([F:15])[F:14])=[C:8]([CH2:10][OH:11])[CH:9]=1.[CH3:17][O:18][CH2:19][CH2:20]Br>CCCCC.CN(C=O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:12][C:13]([F:14])([F:15])[F:16])=[C:8]([CH2:10][O:11][CH2:20][CH2:19][O:18][CH3:17])[CH:9]=1

Participants

6

Reactant 3

HCID 24758Sodium hydride2×HCID 809722-Bromoethyl methyl ether2×HCID 46835523[5-Bromo-2-(trifluoromethoxy)phenyl]methanol

Product 1

HCID 68617899HCID 68617899, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8003PentaneSolvent

Conditions

Temperature
2.5 °C

Procedure

In a 3-neck flask under argon, a 55-65% dispersion of NaH in oil (0.097 g, 2.44 mmol) is washed with n-pentane, the organics are removed and DMF (10 mL) is added. The mixture is cooled to 0-5° C., and a solution of (5-bromo-2-trifluoromethoxy-phenyl)-methanol (0.60 g, 2.21 mmol) in DMF (3.0 mL) is added dropwise. After warming to room temperature, stirring is continued for 1 h before this mixture is added to a solution of 2-bromoethyl methyl ether (0.312 mL, 3.32 mmol) in DMF (3mL). After 4 hrs at room temperature, the reaction is still incomplete by TLC. Another aliquot of NaH (1 equiv; oil dispersion washed with pentane) and 2-bromoethyl methyl ether (0.312 mL, 3.32 mmol) are added, followed by stirring for 18 hrs at room temperature. The mixture is poured into ice-water and extracted with AcOEt, the combined organics are dried (Na2SO4) and evaporated to dryness to give the title compound as yellowish oil. MS: 346.0/348.0 [M+H2l O]+. tR (HPLC, Nucleosil C18HD column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 5.80 min. 1H-NMR (CDCl3): δ 3.49 (s, 3H), 3.64 (m, 2H), 3.72 (m, 2H), 4.69 (s, 2H), 7.13 (dd, 1H), 7.46 (dd, 1H), 7.77 (d, 1H) ppm.

Workup

  1. customthe organics are removed
  2. additionDMF (10 mL) is added
  3. temperatureAfter warming to room temperature
  4. waitAfter 4 hrs at room temperature
  5. stirringby stirring for 18 hrs at room temperature
  6. extractionextracted with AcOEt
  7. dry with materialthe combined organics are dried (Na2SO4)
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-831d1c0f14cd4dc3888128e11090f5f7
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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