Dimethylformamide → 1-Bromo-5-isopropyl-2,4-bis-methoxymethoxy-benzene

HRID 1947173Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[C:5]([OH:11])=[CH:4][C:3]=1[OH:12].CN(C)[CH:15]=[O:16].[CH2:18](N(C(C)C)C(C)C)C.[CH3:27][O:28][CH2:29]Cl>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[C:5]([O:11][CH2:27][O:28][CH3:29])=[CH:4][C:3]=1[O:12][CH2:18][O:16][CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

4-bromo-6-isopropyl-benzene-1,3-diol (IM1-a: 10.5 g, 45.5 mmol), dimethyl formamide (50 mL) and ethyldiisopropylamine (39.6 mL, 227 mmol) were placed in a 100 mL eggplant shaped flask, and the solution was cooled to 0° C., mixed with methoxymethylchloride (17.3 mL, 227 mmol) and the mixture was allowed to come to room temperature. After stirring for 12 hours the solution was heated to 50° C. and stirring was continued further for 6.5 hours. After completing the reaction, ethyl acetate was added, and after washing the organic layer 4 times with saturated sodium chloride, the organic layer was dried anhydrous sodium sulfate. After filtration and evaporation, the residue was purified by silica gel column chromatography to obtain the title compound (IM2-a: 12.1 g, 83.1%).

Workup

customto come to room temperature
temperaturewas heated to 50° C.
stirringstirring
waitwas continued further for 6.5 hours
additionwas added
washafter washing the organic layer 4 times with saturated sodium chloride
filtrationAfter filtration and evaporation
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-0feda5b19cb3441c9966e115d8d35797
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399464B2

Reaction notes

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