Dimethylformamide → HCID 19775687, compound

HRID 1613265Notes

Reaction equation

HRID 1613265 reaction equation
[H-].[Na+].[C:3]1([C:9]2[CH:14]=[CH:13][C:12](O)=[CH:11][CH:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][Cl:21].CN(C)C=[O:25]>>[Cl:21][CH2:20][CH2:19][CH2:18][CH2:17][O:25][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 71034-HydroxybiphenylHCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutane

Product 1

HCID 19775687HCID 19775687, compoundYield 78%

Procedure

To a suspension of sodium hydride (60%, 4.7 g, 117 mmol) in dimethylformamide (400 mL) was added 4-phenylphenol (10 g, 60 mmol) portionwise. The mixture was stirred at room temperature for 2 hours, then 1-bromo-4-chlorobutane (13 mL, 117 mmol) was added, and the mixture allowed to stir at room temperature overnight. The reaction was quenched with methanol (30 mL) and filtered through Celite®. The filtrate was taken up in ether (500 mL), washed thrice with water (250 mL) and dried over sodium sulfate. The solution was concentrated to give 12.2 g (78%) of 4-chlorobutoxy-phenylbenzene as an amber oil. 1H NMR (CDCl3): δ7.61-6.88(m.9H), 4.01(t,2H), 3.62(t.2H), 2.01(m,1H).

Workup

  1. stirringto stir at room temperature overnight
  2. customThe reaction was quenched with methanol (30 mL)
  3. filtrationfiltered through Celite®
  4. washwashed thrice with water (250 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-68fc0e9afe7249d3bc093e89badd5f5e
Source dataset
uspto-grants-1993_03
Patent number
US05192786

Reaction notes

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