Carbon tetrabromide → HCID 19360609, compound

HRID 376977Notes

Reaction equation

[CH2:1]([C:8]([N:26]([CH3:28])[CH3:27])([CH2:24][CH3:25])[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20]O)=[C:13]([O:22][CH3:23])[CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:49]>C(Cl)Cl>[CH2:1]([C:8]([N:26]([CH3:28])[CH3:27])([CH2:24][CH3:25])[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][Br:49])=[C:13]([O:22][CH3:23])[CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

14.3 g (37.1 mmol) of 2-benzyl-2-dimethylamino-1-[4-(3-hydroxy-propoxy)-3-methoxy-phenyl]-butan-1-one are dissolved in 200 ml of methylene chloride, and 10.7 g (40.8 mmol) of triphenylphosphine and 13.5 g (40.8 mmol) of carbon tetrabromide are added at 0° C. successively. The solution is stirred at 0° C. for 0.5 h. Then the solution is concentrated to give the crude product, which is purified by column chromatography on silica gel with ethyl acetate-hexane (20:80) as an eluent. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 0.69 (t, 3H), 1.83-1.92 (m, 1H), 2.03-2.13 (m, 1H), 2.38 (s, 6H), 2.38-2.45 (m, 2H), 3.17-3.25 (m, 2H), 3.64 (t, 2H), 3.88 (s, 3H), 4.22 (t, 2H), 6.86 (d, 1H), 7.15-7.28 (m, 5H), 7.93 (d, 1H), 8.20 (dd, 1H).

Workup

concentrationThen the solution is concentrated

Sources & evidence

ORD record: ord-0186399bb17844248d2167bbc94899d8
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06022906

Reaction notes

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