Water → Tert-butyl 5-bromopentanoate

HRID 661463

Reaction equation

HRID 661463 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20].[C:22](O)([CH3:25])([CH3:24])[CH3:23].O>O1CCCC1.C(OCC)(=O)C>[C:22]([O:20][C:19](=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][Br:14])([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 9845Trifluoroacetic anhydrideHCID 163685-Bromovaleric acid

Product 1

HCID 545791Tert-butyl 5-bromopentanoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-40 °C

Procedure

Trifluoroacetic acid anhydride (7.7 ml) was added dropwise to a solution of 5-bromovaleric acid (5 g) in tetrahydrofuran (25 ml) under nitrogen atmosphere at −40° C. and the solution was stirred at −40° C. for 30 minutes. To the mixture, was added tert-butanol (25 ml) at −40° C. and the stirring was continued for 3 hours while the temperature was gradually raised up to room temperature. Water and ethyl acetate were added to the mixture and the organic layer was separated, washed with a saturated sodium hydrogen carbonate aq. solution three times and then a saturated brine, dried over magnesium sulfate and concentrated in vacuo to give 5-bromovaleric acid tert-butyl ester (5.88 g). MS (m/z): 237/239 [M+H]+.

Workup

  1. waitthe stirring was continued for 3 hours while the temperature
  2. temperaturewas gradually raised up to room temperature
  3. customthe organic layer was separated
  4. washwashed with a saturated sodium hydrogen carbonate aq. solution three times
  5. dry with materiala saturated brine, dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1aefc29c1b2247598d58dca2806df4e3
Source dataset
uspto-grants-2011_12
Patent number
US08084611B2

Linked notes

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