Bis(2-bromoethyl) ether → HCID 66749077, compound

HRID 1868774Notes

Reaction equation

HRID 1868774 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[F:8].Br[CH2:13][CH2:14][O:15][CH2:16][CH2:17]Br.CC([O-])(C)C.[Na+]>CCOCC.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([C:10]#[N:11])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 69572(3,4-Difluorophenyl)acetonitrileHCID 23676156Sodium t-butoxide

Product 1

HCID 66749077HCID 66749077, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture 2-(3,4-difluorophenyl)acetonitrile (25.00 g, 163 mmol) and 2-bromoethyl ether (22.8 mL, 163 mmol) in ether was added dropwise through an addition funnel to a mixture of sodium 2-methylpropan-2-olate (39.2 g, 408 mmol) in DMF (163 mL) at 0° C. The reaction was then allowed to warm to ambient temperature and stirred for 3 hours. The reaction mixture was quenched with 12N HCl, diluted with 400 mL of EtOAc, added to a separatory funnel, partitioned with NaHCO3 (saturated, aqueous), washed 2 times with 100 mL of NaHCO3 (saturated, aqueous), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound which was used without further purification. MS (m/z)=224 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with 12N HCl
  2. additiondiluted with 400 mL of EtOAc
  3. additionadded to a separatory funnel
  4. custompartitioned with NaHCO3 (saturated, aqueous)
  5. washwashed 2 times with 100 mL of NaHCO3 (saturated, aqueous)
  6. customseparated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0adc21a6b22043e8a46ae4646eb5a8ce
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

Loading…