Triphenylphosphine → (3-Bromo-2-methoxyphenyl)methanamine

HRID 561252Notes

Reaction equation

HRID 561252 reaction equation
[OH-].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:22]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Br:32])[C:27]=1[O:33][CH3:34])=[N+]=[N-]>C1COCC1.O>[Br:32][C:28]1[C:27]([O:33][CH3:34])=[C:26]([CH:31]=[CH:30][CH:29]=1)[CH2:25][NH2:22]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 597786811-(Azidomethyl)-3-bromo-2-methoxybenzene

Product 1

HCID 57813384(3-Bromo-2-methoxyphenyl)methanamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.1 g of potassium hydroxide (KOH) and 5.8 g of triphenyl phosphine (Ph3P) were added to a solution of 1-azidomethyl-3-bromo-2-methoxy-benzene 7 in 100 mL of THF and 10 mL of water. The mixture was stirred overnight at room temperature. The mixture was quenched with aqueous concentrated hydrochloride. After standard acid/base aqueous work up, 3.9 g of crude 3-bromo-2-methoxy-benzylamine 8 was obtained (after two steps).

Workup

  1. customThe mixture was quenched with aqueous concentrated hydrochloride

Sources & evidence

ORD record
ord-6bc45ea5a649452e94a45736d7546d0f
Source dataset
uspto-grants-2011_11
Patent number
US08063231B2

Reaction notes

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