Carbon tetrabromide → HCID 22648026, compound

HRID 394116Notes

Reaction equation

HRID 394116 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[Cl:25][C:26]1[C:31](CO)=[C:30]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=2[Cl:41])[CH:29]=[C:28]([Cl:42])[N:27]=1>C(#N)C>[Br:24][CH2:20][C:31]1[C:26]([Cl:25])=[N:27][C:28]([Cl:42])=[CH:29][C:30]=1[C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=1[Cl:41]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22648024HCID 22648024, compound

Product 1

HCID 22648026HCID 22648026, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triphenyl phosphine (0.67 g, 2.55 mol) and carbon tetrabromide (0.85 g, 2.56 mmol) were added to a solution of [2,6-dichloro-4-(2-chloro-4-fluorophenyl)pyridin-3-yl]methanol (2.14 mmol theoretical) in 15 mL acetonitrile at rt. After stirring overnight, the solution was concentrated and the residue partitioned between water and dichloromethane. The organic phase was washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography using ethyl ether/hexanes as the eluent to give 3-(bromomethyl)-2,6-dichloro-4-(2-chloro-4-fluorophenyl)pyridine. Mass spectrum (ESI) 368 (M+1). 1H NMR (500 MHz, CDCl3): δ 4.10(d, 1H, J=10.8 Hz); 4.53(d, 1H, J=10.6 Hz); 7.17(s, 1H); 7.15-7.21(m, 1H); 7.30-7.34(m, 1H); 7.36-7.41(m, 1H).

Workup

  1. concentrationthe solution was concentrated
  2. customthe residue partitioned between water and dichloromethane
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-75fae591c3964ff6b5f5bfc07a47d96c
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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