1-Bromo-4-ethylbenzene → HCID 69200004, compound

HRID 2219457Notes

Reaction equation

HRID 2219457 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1O)[C:6]([O:8][CH3:9])=[O:7])=[O:2].[CH2:14]([C:16]1[CH:21]=[CH:20][C:19]([Li])=[CH:18][CH:17]=1)[CH3:15].C([Li])(C)(C)C.BrC1C=CC(CC)=CC=1.[Cl-].[NH4+]>O1CCCC1>[CH2:14]([C:16]1[CH:21]=[CH:20][C:19]([CH:1]([OH:2])[C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=2)[C:6]([O:8][CH3:9])=[O:7])=[CH:18][CH:17]=1)[CH3:15]

Participants

7

Reactant 5

HCID 153131-Bromo-4-ethylbenzeneHCID 25517Ammonium ChlorideHCID 212595Benzoic acid, 3-formyl-4-hydroxy-, methyl esterHCID 178418306HCID 178418306, compoundHCID 178506701HCID 178506701, compound

Product 1

HCID 69200004HCID 69200004, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of methyl 3-formyl-4-hydroxybenzoate (4.0 g, 22.2 mmol) and tetrahydrofuran (100 mL), 4-ethylphenyllithium [which had been prepared by stirring t-butyllithium (66 mmol) into a mixture of 1-bromo-4-ethylbenzene (12.3 g, 66 mmol) and tetrahydrofuran (200 mL) at −70° C. for 30 minutes] was added at −70° C. and stirred for 1 hour. After addition of saturated aqueous ammonium chloride, the reaction mixture was extracted with ethyl acetate, and the organic phase was washed with saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=65:35-50:50) to give methyl 3-[(4-ethylphenyl)hydroxymethyl]benzoate (2.92 g, 46%) as a light-yellow gum.

Workup

  1. customhad been prepared
  2. additionwas added at −70° C.
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washthe organic phase was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter the solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=65:35-50:50)

Sources & evidence

ORD record
ord-ea9672eff7e24d7d86aef0c5bcc8758e
Source dataset
uspto-grants-2008_08
Patent number
US07414072B2

Reaction notes

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