Triphenylphosphine → 5-(3-(Bromomethyl)-4-methoxyphenyl)-2-methyl-2H-tetrazole

HRID 391397Notes

Reaction equation

HRID 391397 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[N:11][N:12]([CH3:14])[N:13]=2)=[CH:5][C:4]=1[CH2:15]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:36]N1C(=O)CCC1=O>C(Cl)Cl>[Br:36][CH2:15][C:4]1[CH:5]=[C:6]([C:9]2[N:10]=[N:11][N:12]([CH3:14])[N:13]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 58993522(2-Methoxy-5-(2-methyl-2H-tetrazol-5-yl)phenyl)methanol

Product 1

HCID 589936045-(3-(Bromomethyl)-4-methoxyphenyl)-2-methyl-2H-tetrazoleYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(2-Methoxy-5-(2-methyl-2H-tetrazol-5-yl)phenyl)methanol (100 mg, 0.45 mmol) and triphenylphosphine (238 mg, 0.9 mmol) were combined in methylene chloride (3 mL) and cooled to 0° C. N-Bromosuccinimide (170 mg, 0.95 mmol) was introduced in portions and the reaction allowed to warm to room temperature. After 16 h, the reaction mixture was diluted with methylene chloride and washed with concentrated sodium bicarbonate (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (30% ethyl acetate/hexanes) gave 80 mg (63%) of the desired material. LC/MS (HPLC method 3): tR=2.69 min, 285.02 (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

Sources & evidence

ORD record
ord-fa5b11985ca94f9cb00fd6915bb44abb
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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