(1-Bromo-2,2-dimethylpropyl)benzene → HCID 87316481, compound

HRID 1844379Notes

Reaction equation

Br[CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([CH3:6])([CH3:5])[CH3:4].[C:13]([O-:16])(=[S:15])[CH3:14].[K+]>CN(C=O)C>[CH3:4][C:3]([CH3:6])([CH3:5])[CH:2]([S:15][C:13](=[O:16])[CH3:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

(1-Bromo-2,2-dimethyl-propyl)-benzene (1.00 g, 4.40 mmol) was dissolved in dry DMF (5 mL) under an argon atmosphere. Potassium thioacetate (2.51 g, 22.0 mmol) was added and the reaction was heated to 50° C. for 7 days. The solution was then concentrated and the product purified by column chromatography to obtain the desired thioester (970 mg, 99%). TLC (Hexane:CH2Cl2, 7:3 v/v): Rf=0.40. 1H NMR (400 MHz, CDCl3): δ 7.33-7.22 (m, 5H), 4.52 (s, 1H), 2.32 (s, 3H), 1.00 (s, 9H). 13C NMR (100 MHz, CDCl3): δ 193.9 (q), 140.4 (q), 129.0, 127.2, 126.4, 58.7, 34.9 (q), 30.2, 27.6. HRMS (m/z): [M+Na]+ calcd. for C13H18ONaS 245.0976; found, 245.0972.

Workup

concentrationThe solution was then concentrated
customthe product purified by column chromatography

Sources & evidence

ORD record: ord-75eafea52e424fd195bda8cfc61eaa40
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946429B2

Reaction notes

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