2-Bromoethanol → 94283-73-5

HRID 1016755Notes

Reaction equation

BrCCO.OCC[O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH:18]([CH3:20])[CH3:19])[CH:12]=[O:13]>>[OH:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH:18]([CH3:20])[CH3:19])[CH:12]=[O:13]

Participants

Reactant 2

HCID 108982-Bromoethanol

HCID 220399183-(2-Hydroxyethoxy)-4-(1-methylethoxy)benzaldehyde

Product 1

HCID 1545352194283-73-5Yield 75%

Procedure

from 3-hydroxy-4-isopropoxybenzaldehyde (prepared in 75% yield by monoalkylation of 3,4-dihydroxybenzaldehyde with isopropyl bromide and K2CO3 in DMF) and 2-bromoethanol there was obtained 3-(2-hydroxy-ethoxy)-4-isopropoxy-benzaldehyde, which was subsequently converted by reaction with 4-aminobenzonitrile and toluene-4-sulphonyl methylisocyanide into methyl (RS)-(4-cyano-phenylamino)-[3-(2-hydroxy-ethoxy)-4-isopropoxy-phenyl]-acetate and then into methyl (RS)-(4-carbamimidoyl-phenylamino)-[3-(2-hydroxy-ethoxy)-4-isopropoxy-phenyl]-acetate hydrochloride (1:1);

Sources & evidence

ORD record: ord-4d7d6d7e249a40f68fcc08ef6ccfcdef
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06476264B2

Reaction notes

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