Ethyl 4-(4-bromobenzoyl)benzoate → HCID 67341340, compound

HRID 1669281Notes

Reaction equation

HRID 1669281 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)[CH3:2].[CH2:21]([Mg]Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C1COCC1>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:6]=[CH:7][C:8]([C:11]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)([OH:19])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:9][CH:10]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24722740Ethyl 4-(4-bromobenzoyl)benzoateHCID 178444609HCID 178444609, compound

Product 1

HCID 67341340HCID 67341340, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-Bromo-benzoyl)-benzoic acid ethyl ester (2.0 g, 6 mmol) in THF (20 mL) at 0° C. is added hexylmagnesium bromide (2M, 3.3 mL). After stirring at room temperature for 2 hours, it is quenched with saturated ammonium chloride, extracted with EtOAc. The organic is concentrated and purified by column chromatography to give 4-[1-(4-Bromo-phenyl)-1-hydroxy-heptyl]-benzoic acid ethyl ester (0.48 g, 19%), which is taken into methanol (2 mL), treated with sodium hydroxide (5N aqueous, 1 mL) for 3 h at room temperature. The mixture is concentrated, diluted with ethyl acetate, acidified with 5 N HCl (1.1 mL), extracted with ethyl acetate. The organic layers are dried and concentrated giving to afford the titled compound (0.47 g).

Workup

  1. customit is quenched with saturated ammonium chloride
  2. extractionextracted with EtOAc
  3. concentrationThe organic is concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-602d730a90ea482995583c873a041139
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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