Triphenylphosphine → 2-(Bromomethyl)-1-(1-methoxycyclohexyl)-4-(trifluoromethyl)benzene

HRID 2075099Notes

Reaction equation

HRID 2075099 reaction equation
[CH3:1][O:2][C:3]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=2[CH2:19]O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[Br:21]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:21][CH2:19][C:10]1[CH:11]=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=[CH:14][C:9]=1[C:3]1([O:2][CH3:1])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 58968721HCID 58968721, compound

Product 1

HCID 589687252-(Bromomethyl)-1-(1-methoxycyclohexyl)-4-(trifluoromethyl)benzeneYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-(1-methoxycyclohexyl)-5-(trifluoromethyl)phenyl)methanol (27 mg; 0.094 mmol) in methylene chloride (1 mL) was added N-bromosuccinimide (28 mg; 0.157 mmol) followed by triphenylphosphine (40 mg; 0.152 mmol). The reaction was stirred at room temperature for 4 hours. The reaction was directly loaded onto silica and purified over 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 5-40% ethyl acetate in heptane) to give 26 mg (79%) of a gum. MS-GC (El): Calc: 351.2, Found; 352 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 7.81 (d, J=1.66 Hz, 1H), 7.48 (td, J=8.30, 1.66 Hz, 1H), 7.39 (d, J=8.30 Hz, 1H), 5.12 (s, 2H), 3.00 (s, 3H), 2.25 (d, J=12.45 Hz, 2H), 1.84-1.71 (m, 3H), 1.65 (m, 4H), 1.27(m, 1H).

Workup

  1. custompurified over 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 5-40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-a65b596752cd48d7919810efc50a00c1
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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