Carbon tetrabromide → HCID 58968695, compound

HRID 2075109Notes

Reaction equation

HRID 2075109 reaction equation
[CH3:1][O:2][C:3]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=2[CH2:18]O)[CH2:7][CH2:6][CH2:5][CH2:4]1.C(Br)(Br)(Br)[Br:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:21][CH2:18][C:9]1[CH:10]=[C:11]([C:14]([F:17])([F:16])[F:15])[CH:12]=[CH:13][C:8]=1[C:3]1([O:2][CH3:1])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67091681HCID 67091681, compound

Product 1

HCID 58968695HCID 58968695, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-(1-methoxycyclopentyl)-5-(trifluoromethyl)phenyl)methanol (10 mg, 0.036 mmol) in anhydrous dichloromethane (5 mL) was added carbon tetrabromide (14.5 mg, 0.043 mmol) followed by triphenylphosphine (11.47 mg, 0.043 mmol). The mixture was stirred at room temperature for 72 hours then the solvent was removed under reduced pressure. The residue was diluted with dichloromethane and hexanes, placed on 1 g of silica gel (Bakerbond spe disposable extraction columns, Mallinkrodt Baker Inc. Phillipsburg, N.J.) and eluted with hexanes to give the title compound (12 mg, 97.6%). 1H NMR (400 MHz, CDCl3) δ 7.78 (s, 1H) 7.46 (d, J=9.1 Hz, 1H) 7.40 (d, J=8.3 Hz, 1H) 4.97 (s, 2H) 2.94 (s, 3H) 2.30 (m, 2H) 2.0 (m, 2H) 1.85 (m, 2H) 1.74 (m, 2H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionThe residue was diluted with dichloromethane and hexanes
  3. washeluted with hexanes

Sources & evidence

ORD record
ord-9785e91d4ae049409cd3910fc94cb694
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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