Citric Acid → 2-(4-(Heptyloxy)phenyl)-2-oxoethyl 4-bromobenzoate

HRID 716419Notes

Reaction equation

HRID 716419 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:7][CH:6]=1)=[O:4].[Br:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.CC(=O)OCC>C(#N)C>[Br:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([O:26][CH2:2][C:3]([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:7][CH:6]=2)=[O:4])=[O:25])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 114644-Bromobenzoic acidHCID 539091862-Bromo-1-(4-(heptyloxy)phenyl)ethanone

Product 1

HCID 866896872-(4-(Heptyloxy)phenyl)-2-oxoethyl 4-bromobenzoateYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-bromo-1-(4-(heptyloxy)phenyl)ethanone INT-4 (1.3 g, 4.2 mmol) and 4-bromobenzoic acid (0.70 g, 3.5 mmol) in ACN (30 mL) was added TEA (0.72 ml, 5.2 mmol). After stirring overnight, the mixture was poured onto aq. citric acid and EA then stirred for 10 min before the solid was collected by filtration. The cake was washed with water and iso-hexanes then dried to provide 905 mg (57%) of 2-(4-(heptyloxy)phenyl)-2-oxoethyl 4-bromobenzoate. LCMS-ESI (m/z) calculated for C22H25BrO4: 432.1. found 433.2 [M+H]+, tR=3.24 min (Method 8).

Workup

  1. stirringthen stirred for 10 min before the solid
  2. filtrationwas collected by filtration
  3. washThe cake was washed with water and iso-hexanes
  4. customthen dried

Sources & evidence

ORD record
ord-c369a5c1799148f19df2af0175f44c89
Source dataset
uspto-grants-2015_11
Patent number
US09187522B2

Reaction notes

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