Hydrogen Bromide → 5-Bromo-3,3-dimethylpentanoic Acid

HRID 1683333Notes

Reaction equation

HRID 1683333 reaction equation
[BrH:1].C1C2C(=CC=CC=2)CCC1.BrBr.[CH3:14][C:15]([CH3:22])([CH:20]=[CH2:21])[CH2:16][C:17]([OH:19])=[O:18].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[Br:1][CH2:21][CH2:20][C:15]([CH3:22])([CH3:14])[CH2:16][C:17]([OH:19])=[O:18]

Participants

6

Reactant 5

HCID 260Hydrogen BromideHCID 7187Benzoyl PeroxideHCID 8404TetralinHCID 24408BromineHCID 106304993,3-Dimethylpent-4-enoic acid

Product 1

HCID 221191285-Bromo-3,3-dimethylpentanoic Acid

Conditions

Temperature
-10 °C

Procedure

A stream of dry hydrogen bromide gas (made from 83.3 m) of tetralin and 71 ml of bromine) was bubbled through a stirred solution of 3,3-dimethylpent-4-enoic acid (80 g, 0.625 mol) in dry light petroleum b.p. 40°-60° C. (940 ml) together with benzoyl peroxide (6.4 g, 0.025 mol) until it was saturated (about 2 hours) whilst the reaction mixture was maintained at the temperature between 10°-20° C. by occasional cooling. After completion of the reaction, the mixture was cooled down to -10° C. and the solid product was collected (near quantitative yield). The product was sufficiently pure by NMR spectroscopy to be used directly in the next step synthesis. However, a pure product was obtained after recrystallised from light petroleum spirit m.p. 53°-55° C. 1H NMR δ3.43 (2H, t), 2.27 (2H, s), 2.10 (2H, t), and 1.08 (6H, s).

Workup

  1. custom(about 2 hours)
  2. temperaturewas maintained at the temperature between 10°-20° C. by occasional cooling
  3. customAfter completion of the reaction
  4. customthe solid product was collected (near quantitative yield)
  5. customto be used directly in the next step synthesis
  6. customHowever, a pure product was obtained
  7. customafter recrystallised from light petroleum spirit m.p. 53°-55° C

Sources & evidence

ORD record
ord-5f52a43b28ae42a585b1236c4dd9c879
Source dataset
uspto-grants-1997_06
Patent number
US05637718

Reaction notes

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