Allyl bromide → HCID 59557775, compound

HRID 1175249Notes

Reaction equation

HRID 1175249 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:18])=[C:6]([CH:17]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=1.[CH2:19](Br)[CH:20]=[CH2:21].[OH-].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:21]([O:16][CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][C:6]2[CH:17]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[Cl:18])=[CH:9][CH:10]=1)[CH:20]=[CH2:19]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 595577662-(4-(5-Bromo-2-chlorobenzyl)phenyl)ethanol

Product 1

HCID 59557775HCID 59557775, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-(4-(5-bromo-2-chlorobenzyl)phenyl)ethanol (intermediate BH) (245 mg, 0.75 mmol), allyl bromide (2.6 mL, 3.01 mmol), potassium hydroxide (84 mg, 1.5 mmol) and tetra-n-butylammonium iodide (13.9 mg, 0.037 mmol) was stirred at room temperature for 6 h. Water (1 mL) was added and extracted with chloroform (3×1 mL), washed with brine (1 mL) and dried (Na2SO4), filtered and evaporated. Preparative TLC using 10:1 hexane:EtOAc gave intermediate BI (246 mg, yield 89%). 1H NMR (300 MHz, CDCl3): δ 7.26-7.08 (m, 7H), 5.90 (m, 1H), 5.22 (m, 2H), 4.02 (s, 2H), 3.99 (m, 2H), 3.64 (t, J=6.9, 7.2 Hz, 2H), 2.89 (t, J=6.9, 7.2 Hz, 2H).

Workup

  1. extractionextracted with chloroform (3×1 mL)
  2. washwashed with brine (1 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customEtOAc gave intermediate BI (246 mg, yield 89%)

Sources & evidence

ORD record
ord-70848c33ff914df4b084b195aed3b6fa
Source dataset
uspto-grants-2010_11
Patent number
US07838499B2

Reaction notes

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