4-Bromobenzoyl chloride → Tert-butyl 4-bromobenzoate

HRID 1694826Notes

Reaction equation

HRID 1694826 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][C:12]([CH3:15])([O-:14])[CH3:13].[K+]>C1COCC1.C(OCC)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:14][C:12]([CH3:15])([CH3:13])[CH3:11])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 685154-Bromobenzoyl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 11334366Tert-butyl 4-bromobenzoateYield 95.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromobenzoyl chloride (25.08 g, 114 mmol) in THF (120 mL) at ±78° C. was added potassium tert-butoxide (120 mL, 1 M in THF, 120 mmol). The reaction mixture was warmed from −78° C. to room temperature over 2 h, and diluted with diethyl ether. The organic phase was washed with saturated NaHCO3 (2×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (5% ethyl acetate in hexanes) gave tert-butyl 4-bromobenzoate (27.96 g, 95%) as a colorless oil: 1H NMR (600 MHz, CDCl3) δ 7.84 (d, J=8.5 Hz, 2H), 7.54 (d, J=8.5 Hz, 2H), 1.59 (s, 9H); ESIMS calcd 257.0 (M++H), found 257.1 (M++H).

Workup

  1. temperatureThe reaction mixture was warmed from −78° C. to room temperature over 2 h
  2. washThe organic phase was washed with saturated NaHCO3 (2×), brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash column chromatography on silica gel (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4657b0404047444780e6e600935eaaff
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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