tert-Butanol → tert-Butyl 2-bromobenzoate

HRID 2244254Notes

Reaction equation

HRID 2244254 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:11][C:12]([OH:15])([CH3:14])[CH3:13]>C(OCC)C.CN(C)C1C=CN=CC=1>[C:12]([O:15][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[Br:1])([CH3:14])([CH3:13])[CH3:11]

Participants

5

Reactant 2

HCID 6386tert-ButanolHCID 235422-Bromobenzoyl chloride

Product 1

HCID 3804415tert-Butyl 2-bromobenzoateYield 52.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-bromobenzoyl chloride 2.0 g, 9.11 mmol) in dry diethyl ether (40 mL) was added 2-methyl-2-propanol (0.96 mL, 10.02 mmol) followed by 4-(dimethylamino)pyridine (111 mg, 0.911 mmol) and the reaction mixture stirred at room temperature under nitrogen for 48 hours. The resulting white suspension was then partitioned between ethyl acetate (100 mL) and 1 M hydrochloric acid (100 mL). The organic phase was separated, washed with 1 M hydrochloric acid (100 mL), 2 M sodium hydroxide (2×100 mL), water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a yellow oil. Purification by flash chromatography using ethyl acetate/hexane as eluant gave the title compound (1.22 g, 52%) as a colorless oil.

Workup

  1. customThe resulting white suspension was then partitioned between ethyl acetate (100 mL) and 1 M hydrochloric acid (100 mL)
  2. customThe organic phase was separated
  3. washwashed with 1 M hydrochloric acid (100 mL), 2 M sodium hydroxide (2×100 mL), water (100 mL) and brine (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-f8bf621cfaf748a4957e5e14d070af57
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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