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ChemicalBook CAS DataBase List 1-(4-bromophenyl)-3-methylbutan-1-one
131895-07-3

1-(4-bromophenyl)-3-methylbutan-1-one synthesis

7synthesis methods
-

Yield:131895-07-3 91%

Reaction Conditions:

in tetrahydrofuran at 0 - 20;

Steps:

I -(4-Bromophenyl)-3-methylbutan-1 -one

A solution of 4-bromo-N-methoxy-N-methylbenzamide Intermediate 84, 1.0 g (4.10 minol) wasdissolved in tetrahydrofuran, 40 mL, was cooled at 00 C and isobutyl magnesium bromide, 8.2mL (8.2 minol) was added and the reaction was stirred at room temperature overnight. The reaction was quenched by addition of a saturated solution of aminonium chloride and extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate, filtered and concentrated under vacuum. Purification by flash silica chromatography 60 (eluent: heptanedichloromethane 1:1) gave Intermediate 85, 900 mg (91%) as a colourless solid.1H NMR (300 MHz, CDCI3): 6 [ppm] = 0.97 (d, 6H), 2.26 (m, IH), 2.77 (d, 2H), 7.58 (d, 2H), 7.80 (d, 2H).U PLC-MS (Method 3): R = 0.97 min., 96%. MS (ESIpos): mz = [M÷H] 241 243.

References:

WO2018/86703,2018,A1 Location in patent:Page/Page column 252; 253