Benzyl Bromide → 4-Benzyloxy-2-nitroaniline

HRID 1281734Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CC(C)([O-])C.[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[CH2:18]([O:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Amino-3-nitrophenol (25 g, 162.2 mmol) was dissolved in DMF and cooled to 0° C. 1M potassium tert-butoxide (162.2 mL) was added dropwise over 20 min. After stirring 30 min at 0° C., benzyl bromide (19.8 mL, 162.2 mmol) in DMF was added dropwise. After 30 min at 0° C., the reaction was quenched with NH4Cl solution. 4-benzyloxy-2-nitroaniline (32 g, 131 mmol) was isolated by filtration. MS(CI, NH3) m/e 245 (M+1)+.

Workup

waitAfter 30 min at 0° C.
customthe reaction was quenched with NH4Cl solution

Sources & evidence

ORD record: ord-7c4d4a5abe6e49c09fa0a4f6517c5b1c
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455522B1

Reaction notes

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