Triphenylphosphine → Methyl 4-(bromomethyl)-2-methylbenzoate

HRID 1364766Notes

Reaction equation

HRID 1364766 reaction equation
O[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH3:13])[CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C(=O)N([Br:40])C(=O)C1>C(Cl)Cl>[Br:40][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH3:13])[CH:4]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 23021531Methyl 4-(hydroxymethyl)-2-methylbenzoate

Product 1

HCID 19372658Methyl 4-(bromomethyl)-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

220 mg of methyl 4-(hydroxymethyl)-2-methylbenzoate was cooled to 0° C. in 5 mL of DCM before adding 260 mg of Triphenylphosphine and 395 mg of NBS. The reaction was concentrated and directly purified via ISCO Combi-Flash to give pure methyl 4-(bromomethyl)-2-methylbenzoate.

Workup

  1. concentrationThe reaction was concentrated
  2. customdirectly purified via ISCO Combi-Flash

Sources & evidence

ORD record
ord-75d4a7b1a9b84941ad6ca9d0bf53b990
Source dataset
uspto-grants-2011_02
Patent number
US07888364B2

Reaction notes

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