Carbon tetrabromide → 7-(bromomethyl)-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydroquinazolin-2(1H)-one

HRID 394112Notes

Reaction equation

HRID 394112 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([CH2:18]O)[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:28])[N:13]2[C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:49]>C(#N)C>[Br:49][CH2:18][C:16]1[CH:15]=[C:14]2[C:9]([CH2:10][NH:11][C:12](=[O:28])[N:13]2[C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:27])=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH:17]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 226479725-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-(hydroxymethyl)-3,4-dihydroquinazolin-2(1H)-one

Product 1

HCID 226481737-(bromomethyl)-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydroquinazolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-(hydroxymethyl)-3,4-dihydroquinazolin-2(1H)-one (500 mg, 1.15 mmol), triphenyl phosphine (363 mg, 1.38 mmol) and carbon tetrabromide (459 mg, 1.38 mmol) in acetonitrile (34 mL) was stirred at rt for 24 h. Removal of the solvent and subsequent purification by flash chromatography using 22% acetone/hexane as eluent provided 7-(bromomethyl)-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydroquinazolin-2(1H)-one as a white solid. 1H NMR (CDCl3, 500 MHz): δ 4.26 (d, 1H, J=14.7 Hz), 4.35 (abq, 2H, J=10.5 Hz), 4.44 (d, 1H, J=14.6 Hz), 5.01 (s, 1H), 6.18 (s, 1H), 6.96 (s, 1H), 7.30-7.60 (m, 7H). MS (API-ES+): 497 (M+H).

Workup

  1. customRemoval of the solvent and subsequent purification by flash chromatography

Sources & evidence

ORD record
ord-631b819951ff4e06a7cc67d0966b7588
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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