Triphenylphosphine → 1-(3-bromomethyl-5-trifluoromethyl-phenyl)-5-methyl-1H-tetrazole

HRID 391412Notes

Reaction equation

HRID 391412 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH2:17]O)[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=2)[N:5]=[N:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:38]N1C(=O)CCC1=O>C(Cl)Cl.C(OCC)(=O)C>[Br:38][CH2:17][C:9]1[CH:8]=[C:7]([N:6]2[C:2]([CH3:1])=[N:3][N:4]=[N:5]2)[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 189421553-(5-Methyltetrazol-1-yl)-5-(trifluoromethyl)phenylmethanol

Product 1

HCID 589934921-(3-bromomethyl-5-trifluoromethyl-phenyl)-5-methyl-1H-tetrazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(3-(5-Methyl-1H-tetrazol-1-yl)-5-(trifluoromethyl)phenyl)methanol (110 mg, 0.46 mmol) and triphenylphosphine (240 mg, 0.93 mmol) were combined in methylene chloride (4 mL) and cooled to 0° C. N-Bromosuccinimide (171 mg, 0.96 mmol) was introduced in portions and the reaction allowed to warm to room temperature. After 16 h, the reaction mixture was diluted with ethyl acetate, washed with concentrated sodium bicarbonate (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (20% ethyl acetate/hexanes) gave 120 mg (82%). LC/MS (HPLC method 3): tR=2.30 min, 323.01 (MH)+.

Workup

  1. temperatureto warm to room temperature
  2. washwashed with concentrated sodium bicarbonate (2×), brine (2×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customColumn chromatography on silica gel (20% ethyl acetate/hexanes) gave 120 mg (82%)

Sources & evidence

ORD record
ord-b7cb8f2a8cc94229a2e2d1974ae4521c
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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