Carbon tetrabromide → HCID 22057733, compound

HRID 1828696Notes

Reaction equation

HRID 1828696 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:8]=[C:7]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17]O)=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:47]>C(Cl)Cl>[Br:47][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][S:9][C:7]2[CH:6]=[CH:5][C:4]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:3]([C:2]([F:26])([F:25])[F:1])[CH:8]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22057742HCID 22057742, compound

Product 1

HCID 22057733HCID 22057733, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [4-(2-trifluoromethyl-biphenyl-4-ylsulfanylmethyl)-phenyl]-methanol (162 mg, 0.4327 mmol, 1 eq.) in anhydrous DCM (5 mL) is added PPh3 (148 mg, 0.5625 mmol, 1.3 eq). The mixture is stirred at room temperature for 5 min. at which point the reaction is cooled to 0° C. To the reaction mixture at 0° C. is added a solution of CBr4 (187 mg, 0.5625 mmol, 1.3 eq.) in anhydrous DCM (2 mL). The reaction is allowed to slowly warm to room temperature and is stirred for 12 h. The reaction mixture is applied directly to silica gel chromatography (6:1 hexanes/EtOAc) to give 4-(4-bromomethyl-benzylsulfanyl)-2-trifluoromethyl-biphenyl.

Workup

  1. temperatureis cooled to 0° C
  2. temperatureto slowly warm to room temperature
  3. stirringis stirred for 12 h

Sources & evidence

ORD record
ord-5c2b51f236934062a0d23ee3eb189640
Source dataset
uspto-grants-2006_06
Patent number
US07060697B2

Reaction notes

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