Carbon tetrabromide → Benzene, 1-(1-bromopropyl)-4-(trifluoromethoxy)-

HRID 594312Notes

Reaction equation

HRID 594312 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10](O)[CH2:11][CH3:12])=[CH:6][CH:5]=1.C(Br)(Br)(Br)[Br:17].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:17][CH:10]([C:7]1[CH:8]=[CH:9][C:4]([O:3][C:2]([F:15])([F:14])[F:1])=[CH:5][CH:6]=1)[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 534664281-(4-(Trifluoromethoxy)phenyl)propan-1-ol

Product 1

HCID 53466431Benzene, 1-(1-bromopropyl)-4-(trifluoromethoxy)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(4-(trifluoromethoxy)phenyl)propan-1-ol (300 mg; 1.36 mmol) in anh. DCM (10 ml) was treated at rt with CBr4 (451 mg; 1.36 mmol), and with PPh3 (357 mg; 1.36 mmol). The resulting mixture was further stirred at rt, under nitrogen, for 17 h. Concentration to dryness under reduced pressure, and subsequent purification by FC (DCM) afforded 1-(1-bromopropyl)-4-(trifluoromethoxy)benzene as a slightly yellow oil which was directly used for the next reaction. LC-MS (conditions A): tR=1.01 min.; no ionisation.

Workup

  1. concentrationConcentration to dryness
  2. customunder reduced pressure, and subsequent purification by FC (DCM)

Sources & evidence

ORD record
ord-446a37434e1f4636be99471e59c81843
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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