1,3-Dibromopropane → HCID 92135508, compound

HRID 925120

Reaction equation

HRID 925120 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:23][CH2:24][CH2:25]Br>ClCCl.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:16]#[N:17])[CH2:25][CH2:24][CH2:23]2)=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 14798Sodium HydroxideHCID 2979634-Benzyloxy-3-methoxyphenylacetonitrile

Product 1

HCID 92135508HCID 92135508, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-(benzyloxy)-3-methoxyphenyl)acetonitrile (3.1 g, 12.24 mmol) in dichloromethane (30 mL) was added sodium hydroxide (30 mL, 50% aqueous solution, 367 mmol), TBAB (0.99 g, 3.06 mmol) and then with 1,3-dibromopropane (2 mL, 19.58 mmol). The reaction was stirred at room temperature for 72 hours. The layers were separated, organic layer was dried (MgSO4) and concentrated. Purification by flash chromatography (silica gel, 5-25% EtOAc/hexane) afforded 1-(4-(benzyloxy)-3-methoxyphenyl)cyclobutanecarbonitrile (1.8 g, 50%). MS (ESI) m/z 294 (M+H)+.

Workup

  1. customThe layers were separated
  2. dry with materialorganic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customPurification by flash chromatography (silica gel, 5-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-4ba382dbcae64e058b3315ac9ebb5dd1
Source dataset
uspto-grants-2016_03
Patent number
US09284272B2

Linked notes

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