Carbon tetrabromide → HCID 10734086, compound

HRID 1987391Notes

Reaction equation

HRID 1987391 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[CH2:15]O)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:19][CH2:15][C:11]1[N:10]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:17])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH:14]=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 10562764HCID 10562764, compound

Product 1

HCID 10734086HCID 10734086, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the above alcohol (0.55 g, 2.17 mmol) and CBr4 (1.08 g, 3.26 mmol) in CH2Cl2 (25 mL) at 0° C. was added a solution of triphenylphosphine (0.68 g, 2.60 mmol) in CH2Cl2 (10 mL) as described in J. Med. Chem. (1997) 40, 14:2196. Purification by flash column chromatography using 25% EtOAc/hexanes afforded 2-bromomethyl-1-(toluene-4-sulfonyl)-1H-imidazole as a yellow oil (0.31 g, 45%). 1H NMR (CDCl3) δ 2.45 (s, 3H), 4.81 (s, 2H), 7.04 (s, 1H), 7.37 (d, 2H, J=9.0 Hz), 7.42 (s, 1H), 7.92 (d, 2H, J=9.0 Hz).

Workup

  1. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-df2fe873b26e412cb346f756d420dcfe
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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