Thionyl Chloride → 5-Bromo-3,3-dimethylpentanoyl chloride

HRID 1683334Notes

Reaction equation

HRID 1683334 reaction equation
[Br:1][CH2:2][CH2:3][C:4]([CH3:10])([CH3:9])[CH2:5][C:6](O)=[O:7].S(Cl)([Cl:13])=O>>[Br:1][CH2:2][CH2:3][C:4]([CH3:10])([CH3:9])[CH2:5][C:6]([Cl:13])=[O:7]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 221191285-Bromo-3,3-dimethylpentanoic Acid

Product 1

HCID 190434955-Bromo-3,3-dimethylpentanoyl chlorideYield 89%

Procedure

5-Bromo-3,3-dimethylpentanoic acid (40 g, 0.192 mol) was converted into the corresponding acid chloride by heating it on a water bath with thionyl chloride (29.6 g, 1.3 equivalents). The title compound was obtained by vacuum distillation as a colourless liquid, 38.8 g (89% yield), b.p. 77° C./0.75 mm Hg. 1H NMR (CDCl3) δ3.40 (2H, t), 2.85 (2H, s), 2.00 (2H, t), and 1.10 (6H, s).

Sources & evidence

ORD record
ord-10ea3feb17fb4659809be4356b6daee4
Source dataset
uspto-grants-1997_06
Patent number
US05637718

Reaction notes

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