tert-Butanol → tert-Butyl 2-bromobenzoate

HRID 274592Notes

Reaction equation

HRID 274592 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C1(N=C=NC2CCCCC2)CCCCC1.[C:26](O)([CH3:29])([CH3:28])[CH3:27]>CN(C)C1C=CN=CC=1.CCOCC>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:5]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 69402-Bromobenzoic acidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 3804415tert-Butyl 2-bromobenzoateYield 77,710.203%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of o-bromobenzoic acid (1 g), N, N'-dicyclohexyl carbodiimide (1.129 g), t-butanol (405 mg) and 4-dimethylaminopyridine (61 mg) in dry ether (20 ml) was stirred at room temperature for 18 h. The resulting precipitate was filtered off and the filtrate evaporated to give a colourless solid which was triturated under petroleum ether (40°-600°) (20 ml) and filtered. The filtrate was evaporated to give a pale yellow oil (0,994 g). b.p. 80°-84°/0.35 mmHg.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. customthe filtrate evaporated
  3. customto give a colourless solid which
  4. customwas triturated under petroleum ether (40°-600°) (20 ml)
  5. filtrationfiltered
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-fe5be31c5b804969b55b6f3c62d68db1
Source dataset
uspto-grants-1995_02
Patent number
US05389659

Reaction notes

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