Carbon tetrabromide → 3-(Bromomethyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]([F:39])([F:38])[S:22]([O:25][C:26]1[C:35]([CH2:36]O)=[CH:34][C:33]2[CH2:32][CH2:31][CH2:30][CH2:29][C:28]=2[CH:27]=1)(=[O:24])=[O:23].C(Br)(Br)(Br)[Br:41]>C(Cl)Cl>[F:20][C:21]([F:39])([F:38])[S:22]([O:25][C:26]1[C:35]([CH2:36][Br:41])=[CH:34][C:33]2[CH2:32][CH2:31][CH2:30][CH2:29][C:28]=2[CH:27]=1)(=[O:24])=[O:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Triphenylphosphine (46.8 mg, 0.178 mmol) was added to a stirred solution of 3-(hydroxymethyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (46.1 mg, 0.149 mmol) and carbon tetrabromide (59.2 mg, 0.178 mmol) in dry CH2Cl2 (1 mL) at 0° C. under N2. The reaction mixture was loaded directly onto a column and purified by flash chromatography (Si, 12×160 mm, 0-20% EtOAc in hexanes gradient) to afford 3-(bromomethyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate, as a colorless solid. Rf=0.95 (20% EtOAc/hexanes). 1H NMR (600 MHz, CDCl3): δ 7.21 (s, 1H); 7.01 (s, 1H); 4.48 (s, 2H); 2.81-2.74 (m, 4H); 1.83-1.78 (m, 4H).
Workup
- custompurified by flash chromatography (Si, 12×160 mm, 0-20% EtOAc in hexanes gradient)
Sources & evidence
- ORD record
- ord-22837b4ffda7425da1bedb927882c6e4
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07910592B2
Reaction notes
Loading…