Water → Ethyl 2-(bromomethyl)-4-tert-butylbenzoate

HRID 1772068Notes

Reaction equation

HRID 1772068 reaction equation
[C:1]([C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>C1C=CC=CC=1>[Br:17][CH2:16][C:7]1[CH:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[CH:15]=[CH:14][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 66610784Ethyl 4-tert-butyl-2-methylbenzoate

Product 1

HCID 66610253Ethyl 2-(bromomethyl)-4-tert-butylbenzoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 100 mL round bottom flask charged with ester 101b (230 mg, 1.04 mmol), N-bromosuccinimide (214 mg, 1.2 mmol), benzoyl peroxide (25 mg, 0.1 mmol) in benzene (5 mL). After the mixture was stirred at reflux for 4 h, H2O (10 mL) was added. The aqueous phase was extracted with CH2Cl2 (2×10 mL), and the combined organic extracts were washed with brine (10 mL), dried with Na2SO4 and concentrated. The crude 101c (287 mg, 92%) was used without further purification.

Workup

  1. temperatureat reflux for 4 h
  2. extractionThe aqueous phase was extracted with CH2Cl2 (2×10 mL)
  3. washthe combined organic extracts were washed with brine (10 mL)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. customThe crude 101c (287 mg, 92%) was used without further purification

Sources & evidence

ORD record
ord-b1ac91f79b1245ec9542eb8af05b1c44
Source dataset
uspto-grants-2016_02
Patent number
US09249123B2

Reaction notes

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