1-[4-(Heptyloxy)phenyl]ethanone → 2-Bromo-1-(4-(heptyloxy)phenyl)ethanone

HRID 716394Notes

Reaction equation

HRID 716394 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[Br-:18].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>C1COCC1>[Br:18][CH2:16][C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:10][CH:11]=1)=[O:17]

Participants

4

Reactant 2

HCID 5779441-[4-(Heptyloxy)phenyl]ethanoneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 539091862-Bromo-1-(4-(heptyloxy)phenyl)ethanoneYield 137.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 1-(4-(heptyloxy)phenyl)ethanone (500 mg, 2.13 mmol) in THF (8.5 mL) under nitrogen was added phenyltrimethylammonium tribromide (842 mg, 2.24 mmol). The reaction mixture was stirred at RT for 2 h, filtered under vacuum and the captured solid washed with THF. The combined liquors were concentrated to afford 919 mg (100%) of 2-bromo-1-(4-(heptyloxy)phenyl)ethanone INT-4 as a yellow oil. LCMS-ESI (m/z) calculated for C15H21BrO2: 313.2. found 313.0 [M+H]+, tR=2.12 min. (Method 4).

Workup

  1. filtrationfiltered under vacuum
  2. washthe captured solid washed with THF
  3. concentrationThe combined liquors were concentrated

Sources & evidence

ORD record
ord-4a20dc984a82489dbf1d2d57a71a2d1b
Source dataset
uspto-grants-2015_11
Patent number
US09187522B2

Reaction notes

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