3',4',5'-Trimethoxyacetophenone → 2-Bromo-1-(3,4,5-trimethoxyphenyl)ethanone

HRID 1441137Notes

Reaction equation

HRID 1441137 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[CH:5]=1)=[O:3].[Br:16]Br>COC.C(Cl)(Cl)Cl>[Br:16][CH2:1][C:2]([C:4]1[CH:5]=[C:6]([O:14][CH3:15])[C:7]([O:12][CH3:13])=[C:8]([O:10][CH3:11])[CH:9]=1)=[O:3]

Participants

5

Reactant 2

HCID 143453',4',5'-TrimethoxyacetophenoneHCID 24408Bromine

Product 1

HCID 36857322-Bromo-1-(3,4,5-trimethoxyphenyl)ethanone

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8254Dimethyl EtherSolvent

Procedure

A mixture of 3.0 g of 3,4,5-trimethoxyacetophenone in 70 ml of dimethyl ether and 30 ml of chloroform is cooled to 0° and then treated with a mixture containing 0.73 ml of bromine in 15 ml of chloroform in a dropwise manner. The reaction mixture is allowed to warm to 20°- 25° and stirred for 1 hr. The reaction mixture is partitioned between chloroform and water. The organic layer is separated, washed with dilute sodium bicarbonate, washed with saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product (4.31 g) is recrystallized from ethanol/water. The solid is isolated and dried (18 hours, 0.01 mm, 40°) to give the title compound, mp 61°-62°; IR (mineral oil) 3010, 2995, 2952, 2926, 2868, 2855, 1695, 1687, 1586, 1505, 1466, 1455, 1428, 1417, 1389, 1335, 1255, 1229, 1190, 1151, 1128, 1004, 820, 636, and 602 cm-1 ; NMR (CDCl3, TMS) 7.24, 4.43 and 3.93δ; CMR (CDCl3) 190.2, 153.1, 149.9, 143.3, 128.9, 106.5, 60.9, 56.3 and 30.4δ; MS (m/z) M+ =288, other ions at m/z 259, 228, 195, 181, 167, 152, 137, 122, 109, 77, 66 and 53.

Workup

  1. temperatureis cooled to 0°
  2. additiontreated with a mixture
  3. temperatureto warm to 20°- 25°
  4. customThe reaction mixture is partitioned between chloroform and water
  5. customThe organic layer is separated
  6. washwashed with dilute sodium bicarbonate
  7. washwashed with saline
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product (4.31 g) is recrystallized from ethanol/water
  11. customThe solid is isolated
  12. customdried (18 hours, 0.01 mm, 40°)

Sources & evidence

ORD record
ord-4feb10587ed342e0bac0f575c64ba553
Source dataset
uspto-grants-1996_03
Patent number
US05502187

Reaction notes

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