Dimethylformamide → HCID 74892046, compound

HRID 20440Notes

Reaction equation

HRID 20440 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[C:9]([F:21])[CH:8]=1.CN(C)[CH:24]=[O:25]>O1CCCC1>[CH2:14]([O:13][C:11]1[CH:12]=[C:7]([CH:8]=[C:9]([F:21])[CH:10]=1)[CH:24]=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 112545161-(Benzyloxy)-3-bromo-5-fluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 74892046HCID 74892046, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add n-butyl lithium (35 mL, 1.6M, 55.96 mmol) over 15 minutes to 1-bromo-3-fluoro-5-benzyloxy-benzene (14.30 g, 50.87 mmol) in tetrahydrofuran (300 mL) cooled in a dry ice/acetone bath, maintaining the internal temperature <−70°. Stir 30 minutes and add N,N-dimethylformamide (7.44 g, 101.74 mmol). Stir 30 minutes and remove cold bath. After 1 hour, quench with saturated aqueous ammonium chloride. Wash organic layer with water and saturated aqueous sodium chloride. Dry (sodium sulfate), filter and concentrate to an oil. Purify on 120 g silica gel eluting with 100:0 to 90:10 hexanes:ethyl acetate to give 3.75 g (32%) of the desired compound as an oil.

Workup

  1. temperaturecooled in a dry ice/acetone bath
  2. temperaturemaintaining the internal temperature <−70°
  3. stirringStir 30 minutes
  4. customremove cold bath
  5. waitAfter 1 hour
  6. customquench with saturated aqueous ammonium chloride
  7. dry with materialDry (sodium sulfate)
  8. filtrationfilter
  9. concentrationconcentrate to an oil
  10. customPurify on 120 g silica gel eluting with 100:0 to 90:10 hexanes

Sources & evidence

ORD record
ord-11e07caa6e10418d87f8ef7f4f29541e
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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