1-(Bromomethyl)-4-(trifluoromethyl)benzene → HCID 67090471, compound

HRID 2074425Notes

Reaction equation

HRID 2074425 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1.[Br:13][CH2:14][C@H:15]1[C:24]2[C:19](=[C:20]([O:26][CH3:27])[C:21]([CH3:25])=[CH:22][CH:23]=2)[CH2:18][C@@H:17]([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[O:16]1>CN1C(=O)CCC1>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:31]2[CH2:32][CH2:33][CH:28]([C@@H:17]3[CH2:18][C:19]4[C:24](=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=4[O:26][CH3:27])[C@H:15]([CH2:14][Br:13])[O:16]3)[CH2:29][CH2:30]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 67090169HCID 67090169, compound

Product 1

HCID 67090471HCID 67090471, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Add 4-trifluoromethylbenzyl bromide (7.2 g) and NMP (20 mL) to REM bound (1R,3S)-4-(1-bromomethyl-5-methoxy-6-methyl-isochroman-3-yl)-piperidine (2.0 g 0.78 mmol/g of loading) in a 50 mL shaking vessel. Shake the reaction mixture at room temperature overnight, filter and wash three times each with NMP, dichloromethane, methanol, and dichloromethane. To this resin add of dichloromethane (18.6 mL) and of DIEA (1.4 mL). Shake the resulting mixture at room temperature overnight, filter and wash the resin twice each with dichloromethane, methanol, and dichloromethane. Combine the filtrates concentrate and add Amberlite IRA-67 (2.0 g) with of dichloromethane (20 mL). Shake the resulting mixture at room temperature for 4 hours, filter and wash twice each with dichloromethane, methanol, and dichloromethane. Combine the filtrates and concentrate to yield the title compound. CIMS 512.1 (MH+), tR (min)=3.52.

Workup

  1. filtrationShake the reaction mixture at room temperature overnight, filter
  2. washwash three times each with NMP, dichloromethane, methanol, and dichloromethane
  3. additionTo this resin add of dichloromethane (18.6 mL) and of DIEA (1.4 mL)
  4. filtrationShake the resulting mixture at room temperature overnight, filter
  5. washwash the resin twice each with dichloromethane, methanol, and dichloromethane
  6. concentrationconcentrate
  7. additionadd Amberlite
  8. filtrationfilter
  9. washwash twice each with dichloromethane, methanol, and dichloromethane
  10. concentrationconcentrate

Sources & evidence

ORD record
ord-dc735298e8824ffeaac0a5ea7520ec71
Source dataset
uspto-grants-2011_04
Patent number
US07919508B2

Reaction notes

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