Octane → HCID 19101410, compound

HRID 1975258Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[C:6]([Br:9])[C:7]=1[OH:8].[CH3:16][N:17]([CH3:21])[C:18](Cl)=[S:19].CCCCCCCC.CCCCCC.C(OCC)(=O)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[C:6]([Br:9])[C:7]=1[O:8][C:18](=[S:19])[N:17]([CH3:21])[CH3:16]

Participants

Conditions

Temperature: 70 °C

Procedure

Following the procedure of Newman and Karnes, J. Org. Chem. 31, 3980 (1966), a mixture of ethyl 3,5-dibromo-4-hydroxyphenylacetate (20 g, 0.06 mol), from Preparation B, N,N-dimethylthiocarbamoyl chloride (10.9 g, 0.088 mol), and 1,4-diazabicyclo[2 2.2]octane (Dabco™) (13.4 g, 0.12 mol) in 250 mL DMF was heated, with stirring, at 70° C. for one hour. The reaction mixture was cooled and the precipitate (Dabco-HCl salt) removed by filtration and washed well with ethyl acetate. The filtrate was concentrated on a rotary evaporator and the solid collected by filtration, washed well with water and dried in vacuum to obtain ethyl 3,5-dibromo-4-(N,N-dimethylthiocarbamoyloxy)phenylacetate (16 g, 0.037 mol, 62% yield), MP: 93°-95° C. (hexane/ethyl acetate).

Workup

temperaturewas heated
temperatureThe reaction mixture was cooled
customthe precipitate (Dabco-HCl salt) removed by filtration
washwashed well with ethyl acetate
concentrationThe filtrate was concentrated on a rotary evaporator
filtrationthe solid collected by filtration
washwashed well with water
customdried in vacuum

Sources & evidence

ORD record: ord-84d6524222c7406a8b1b89ce60433ba6
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05284971

Reaction notes

Loading…