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

HRID 1802937Notes

Reaction equation

HRID 1802937 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Br)=[O:8])=[CH:5][CH:4]=1.[C:12]([OH:16])([CH3:15])([CH3:14])[CH3:13]>C(Cl)Cl>[C:12]([O:16][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([CH2:2][Br:1])=[CH:4][CH:5]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 46406714-Bromomethyl benzoyl bromide

Product 1

HCID 11414578Tert-butyl 4-(bromomethyl)benzoateYield 53.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromomethylbenzoyl bromide (13.9 g, 50 mmol, 1.0 eq) was added to 50 mL of DCM, followed by t-butanol (9.6 mL, 100 mmol, 2.0 eq) and the mixture was slowly warmed to room temperature. After 20 hours, the reaction was concentrated under reduced pressure, dissolved into 350 mL EtOAc, washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl. The organic was dried over MgSO4, filtered, and concentrated under reduced pressure to yield intermediate (19a) as a semisolid (7.3 g).

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. dissolutiondissolved into 350 mL EtOAc
  3. washwashed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl
  4. dry with materialThe organic was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3f7b94ff9bcb4ca0a16d5d84213f1768
Source dataset
uspto-grants-2013_01
Patent number
US08349875B2

Reaction notes

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