Water → HCID 58045918, compound

HRID 657977Notes

Reaction equation

HRID 657977 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:16][CH2:17][F:18].[H-].[Na+].O>CN(C=O)C>[C:1]([C:5]1[CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=[C:9]([O:11][CH2:16][CH2:17][F:18])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 129822-Fluoroethyl bromideHCID 24758Sodium hydride2×HCID 58045815HCID 58045815, compound

Product 1

HCID 58045918HCID 58045918, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3-tert-Butyl-5-hydroxyphenyl)ethanone (O3.106; 500 mg) was dissolved in DMF (10 ml), and 1-bromo-2-fluoroethane (195 μl) was added while stirring. Sodium hydride (80 mg) was added at RT. After stirring at RT for 3 h, the mixture was left to stand overnight and then further sodium hydride (20 mg) was added and the mixture was stirred for a further 2 h. Then water was added and the mixture was concentrated to dryness. The residue was taken up in EA and washed three times with water. The EA phase was dried over magnesium sulfate, filtered and concentrated. 600 mg of the title compound were obtained. LC-MS rt: 1.13 min [M+H]+: 239.1 (met. b)

Workup

  1. stirringAfter stirring at RT for 3 h
  2. waitthe mixture was left
  3. stirringthe mixture was stirred for a further 2 h
  4. concentrationthe mixture was concentrated to dryness
  5. washwashed three times with water
  6. dry with materialThe EA phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6183c844cd174767877a45f9fb86c304
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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