Benzyl Bromide → (2-(Benzyloxy)-5-nitrophenyl)methanol

HRID 32325Notes

Reaction equation

HRID 32325 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[OH:12].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.COC(O)C1C=C([N+]([O-])=O)C=CC=1OC>>[CH2:13]([O:12][C:4]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[CH2:2][OH:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 27638232-Hydroxy-5-nitrobenzyl alcoholHCID 210144602-Methoxy-5-nitrobenzaldehyde methyl hemiacetal

Product 1

HCID 10264526(2-(Benzyloxy)-5-nitrophenyl)methanolYield 84%

Procedure

This intermediate was prepared by alkylation of 2-hydroxymethyl-4-nitrophenol with benzyl bromide following the method described for preparation of 2-methoxy-5-nitrobenzaldehyde methyl hemiacetal in a yield of 84%: MP 81-83° C.; 1H NMR δ (DMSO-d6, 500 MHz) 8.26 (d, 1H, J=2.9 Hz H-6), 8.15 (dd, 1H, J=2.9 and 9.1 Hz, H-4), 7.46 (d, 2H, J=7.0, 2′, 6′-Hs) 7.41 (dd, 2H, J=7.0 and 7.7, 3′,5′Hs), 7.34 (d, 1H, J=7 Hz, 4′-H), 7.25 (d, 1H, J=9.1 Hz, 3-H), 5.4 (br, 1H, OH), 5.29 (s, 2H, CH2), 4.57 (s, 2H, CH2).

Sources & evidence

ORD record
ord-bcbde38d2ea14b5394b1caa4c7c62767
Source dataset
uspto-grants-2008_09
Patent number
US07427608B2

Reaction notes

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