Water → HCID 19426985, compound

HRID 260420

Reaction equation

HRID 260420 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH2:8][OH:9].[Br:15][C:16]1[CH:21]=[C:20](F)[CH:19]=[C:18]([F:23])[CH:17]=1.O>CN(C=O)C>[Br:15][C:16]1[CH:17]=[C:18]([F:23])[CH:19]=[C:20]([O:9][CH2:8][C:7]2[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:5]([O:4][CH3:3])[CH:6]=2)[CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7118Veratryl alcoholHCID 24758Sodium hydrideHCID 1363131-Bromo-3,5-difluorobenzene

Product 1

HCID 19426985HCID 19426985, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (80% disp. in oil; 933 mg, 31.1 mmol) was added, all at once to 3,4-dimethoxybenzyl alcohol (3.48 g, 20.7 mmol) in DMF (40 mL) at 0° C. and under Ar. After 5 min., the mixture was allowed to warm to r.t. After 1 h, 1-bromo-3,5-difluorobenzene (4 g, 20.7 mmol) in DMF (5 mL) was added dropwise at r.t. The resulting mixture was kept at this temperature for 16 h and slowly poured into H2O (500 mL). It was extracted with EtOAc (3×) and the combined organics were washed with 25% NH4OAc buffer (1×), H2O (2×) and brine. The solution was dried (MgSO4) and concentrated to give a pale yellow solid that was purified by column chromatography on silica gel (EtOAc:hexane, 10:90-15:85) to afford the title compound as a white solid (5.85 g, 83%).

Workup

  1. customat 0° C.
  2. waitAfter 1 h
  3. waitThe resulting mixture was kept at this temperature for 16 h
  4. extractionIt was extracted with EtOAc (3×)
  5. washthe combined organics were washed with 25% NH4OAc buffer (1×), H2O (2×) and brine
  6. dry with materialThe solution was dried (MgSO4)
  7. concentrationconcentrated
  8. customto give a pale yellow solid
  9. customthat was purified by column chromatography on silica gel (EtOAc:hexane, 10:90-15:85)

Sources & evidence

ORD record
ord-3f8c89cd53714150a780ebca024553a9
Source dataset
uspto-grants-1996_06
Patent number
US05527827

Linked notes

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