Carbon tetrabromide → N'-(4-(bromomethyl)-3-chloro-5-fluorophenylsulfonyl)-N,N-dimethylformimidamide

HRID 1627390Notes

Reaction equation

HRID 1627390 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:11]([N:14]=[CH:15][N:16]([CH3:18])[CH3:17])(=[O:13])=[O:12])[CH:5]=[C:6]([F:10])[C:7]=1[CH2:8]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:39]>C(Cl)Cl>[Br:39][CH2:8][C:7]1[C:6]([F:10])=[CH:5][C:4]([S:11]([N:14]=[CH:15][N:16]([CH3:18])[CH3:17])(=[O:13])=[O:12])=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66739970N'-(3-chloro-5-fluoro-4-(hydroxymethyl)phenylsulfonyl)-N,N-dimethylformimidamide

Product 1

HCID 66740034N'-(4-(bromomethyl)-3-chloro-5-fluorophenylsulfonyl)-N,N-dimethylformimidamideYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N′-(3-chloro-5-fluoro-4-(hydroxymethyl)phenylsulfonyl)-N,N-dimethylformimidamide (600 mg, 2 mmol) in DCM (10 mL) at 0° C. were added PPh3 (1.06 g, 4.06 mmol) and CBr4 (1.3 g, 4.06 mmol). The resulting solution was stirred at room temperature for 30 min, concentrated, and purified by column chromatography (silica, DCM/EtOAc=20:1) to afford N′-(4-(bromomethyl)-3-chloro-5-fluorophenylsulfonyl)-N,N-dimethylformimidamide (673 mg, 92%) as ivory solid. 1H NMR (400 MHz, CDCl3) δ 8.18-8.11 (m, 1H), 7.78 (d, 1H), 7.57 (dd, 1H), 4.64 (d, 2H), 3.22 (d, 3H), 3.10 (t, 3H); MS (EI) m/z 379 (M+Na+).

Workup

  1. concentrationconcentrated
  2. custompurified by column chromatography (silica, DCM/EtOAc=20:1)

Sources & evidence

ORD record
ord-c98ee2b7a9534ff9b63d5404b61377b5
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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