3-Bromophenol → HCID 14097602, compound

HRID 569510Notes

Reaction equation

HRID 569510 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.Cl[CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1>CN(C)C=O>[Br:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1

Participants

5

Reactant 3

HCID 115633-BromophenolHCID 203942-(Chloromethyl)quinolineHCID 24758Sodium hydride

Product 1

HCID 14097602HCID 14097602, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 60% sodium hydride (9.8 g, 245 mmol) in 250 mL dimethylformamide at 5° C. under nitrogen is added portionwise 3-bromophenol (42.6 g, 246 mmol). After thirty minutes a solution of 2-(chloromethyl)quinoline (43.6 g, 246 mmol) in 250 mL dimethylformamide is rapidly added. The reaction is allowed to warm to room temperature. After overnight stirring, the reaction is freed of solvent and then partitioned between 1N sodium hydroxide and methylene chloride. The organic layer is separated, dried over magnesium sulfate and evaporated to 67.9 g of a yellow solid. Recrystallization from acetonitrile affords 42.8 g (55%) of brown crystals, m.p. 79°-81° C.

Workup

  1. custompartitioned between 1N sodium hydroxide and methylene chloride
  2. customThe organic layer is separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to 67.9 g of a yellow solid
  5. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-c9825e20cf5d42649fa8fd370e7de28a
Source dataset
uspto-grants-1988_03
Patent number
US04732978

Reaction notes

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