3-Hydroxybenzaldehyde → 2-Bromo-5-hydroxybenzaldehyde

HRID 1181013Notes

Reaction equation

HRID 1181013 reaction equation
NCOC(=O)CCC1C=CC=CC=1.[OH:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19].[Br:23]Br>>[Br:23][C:20]1[CH:21]=[CH:22][C:15]([OH:14])=[CH:16][C:17]=1[CH:18]=[O:19]

Participants

4

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 24408BromineHCID 17984373HCID 17984373, compound

Product 1

HCID 3871792-Bromo-5-hydroxybenzaldehyde

Procedure

Reaction Scheme 9 shows the synthetic route to prepare aminomethyldihydrocinnamate headpiece. 3-Hydroxybenzaldehyde (29) is reacted with bromine to give 2-bromo-5-hydroxybenzaldehyde (30), which is then coupled to t-butylacrylate to give the compound (31). Compound (31) is treated with NH2OH to give oxime (32), which undergoes hydrogenation to give aminomethyldihydrocinnamate (33). Various functional groups (Z2) can be introduced at the aminomethyl portion of compound (33) to afford compound (34).

Workup

  1. customReaction Scheme 9

Sources & evidence

ORD record
ord-2f6d719d7590474499671f41af5f4d59
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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