Dichloromethane → HCID 23114570, compound

HRID 2080528Notes

Reaction equation

HRID 2080528 reaction equation
ClCCl.[Cl:4][C:5]1[C:6]([CH:13]([S:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])=[CH:7][C:8]([CH2:11]O)=[N:9][CH:10]=1.C(Br)(Br)(Br)[Br:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCCCCC>[Br:31][CH2:11][C:8]1[CH:7]=[C:6]([CH:13]([S:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])[C:5]([Cl:4])=[CH:10][N:9]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 23114767HCID 23114767, compound

Product 1

HCID 23114570HCID 23114570, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a dichloromethane (15 ml) solution of the [5-chloro-4-[(4-chlorophenylthio)(2,5-difluorophenyl)methyl]pyridin-2-yl]methanol (582 mg, 1.41 mmol) obtained in Example 256 were sequentially added carbon tetrabromide (936 mg, 2.82 mmol) and triphenylphosphine (407 mg, 1.55 mmol) at 0° C. The resulting mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=20:1 eluate was concentrated under reduced pressure to give the title compound (518 mg, 1.09 mmol, 77%) as a colorless oil.

Workup

  1. customat 0° C
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue thus obtained
  4. concentrationethyl acetate=20:1 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ce2efa56f979487783d0cb7817405a82
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

Loading…