4-Bromoanisole → HCID 178491912, compound

HRID 923713Notes

Reaction equation

HRID 923713 reaction equation
[C:1]([O:5][C:6](=O)N[C@H](C)C(N(OC)C)=O)([CH3:4])([CH3:3])C.[Mg:17].COC1C=CC([Br:26])=CC=1.[I-].O1C[CH2:31][CH2:30][CH2:29]1>>[CH3:6][O:5][C:1]1[CH:3]=[CH:31][C:30]([Mg:17][Br:26])=[CH:29][CH:4]=1

Participants

6

Reactant 5

HCID 77304-BromoanisoleHCID 8028Tetrahydrofuran2×HCID 30165Iodide IonHCID 5462224MagnesiumHCID 23537239N~2~-(tert-Butoxycarbonyl)-N-methoxy-N-methyl-D-alaninamide

Product 1

HCID 178491912HCID 178491912, compound

Procedure

A solution of (R)-t-butyl(1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate (5.0 g, 21.5 mmol) in 50 mL of tetrahydrofuran was cooled to −20° C. 4-Methoxyphenylmagnesium bromide was prepared by stirring magnesium (2.1 g, 86.1 mmol), 4-methoxybromobenzene (16.1 g, 86.1 mmol), and a catalytically effective amount of iodide in 100 mL of tetrahydrofuran, and dropwise added to the solution. A reaction was conducted at 20˜25° C. for 16 hrs while stirring.

Sources & evidence

ORD record
ord-c9f87c68c1364baa8598fb241708ab61
Source dataset
uspto-grants-2016_03
Patent number
US09278996B2

Reaction notes

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