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

HRID 1183570Notes

Reaction equation

HRID 1183570 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-e5b5b8b66bbd4668995b18822e16f61d
Source dataset
uspto-grants-2014_03
Patent number
US08664254B2

Reaction notes

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