tert-Butanol → Tert-butyl 4-(bromomethyl)benzoate

HRID 1721230Notes

Reaction equation

HRID 1721230 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[CH:22]=[CH:21][C:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:12][CH:11]=1.C(O)(C)(C)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:9][C:10]1[CH:22]=[CH:21][C:13]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 7187Benzoyl Peroxide2×HCID 67184N-bromobutanimide2×HCID 116297491,1-Dimethylethyl 4-methylbenzoate

Product 1

HCID 11414578Tert-butyl 4-(bromomethyl)benzoateYield 40%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (NBS) (35.8 g, 0.20 mol) was added in several portions to a solution of 1,1-dimethylethyl 4-methylbenzoate (prepared by the reaction of the respective acid chloride with t-butanol.) (38.0 g, 0.20 mol) and benzoyl peroxide (0.36 g, 1.5 mmol) in carbon tetrachloride (1200 mL) at vigorous reflux. Another portion of benzoyl peroxide (0.36 g, 1.5 mmol) was added just before the final addition of NBS. After the foaming subsided, the reaction mixture was cooled to room temperature, washed with water (2×60 mL) and dried over magnesium sulfate. Filtration and concentration provided an oil that was purified by HPLC on silica gel eluting with a mixture of hexanes and ethyl acetate to give 1,1-dimethylethyl 4-bromomethylbenzoate (21.4 g) in 40% yield.

Workup

  1. washwashed with water (2×60 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationFiltration and concentration
  4. customprovided an oil that
  5. customwas purified by HPLC on silica gel eluting with a mixture of hexanes and ethyl acetate

Sources & evidence

ORD record
ord-58e74c38dbb944c8aa833bef0ae515b3
Source dataset
uspto-grants-1996_04
Patent number
US05508437

Reaction notes

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