Hydrogen Bromide → N-(3-fluoro-4-hydroxyphenyl)-N'-(2-phenylethyl)ethanediamide

HRID 2106123Notes

Reaction equation

HRID 2106123 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:28])[C:17]([NH:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:18])=[CH:11][C:10]=1[F:29])C1C=CC=CC=1.Br>C(O)(=O)C>[F:29][C:10]1[CH:11]=[C:12]([NH:15][C:16](=[O:28])[C:17]([NH:19][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:18])[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 57810151N-(4-benzyloxy-3-fluorophenyl)-N'-(2-phenylethyl)ethanediamide

Product 1

HCID 57810404N-(3-fluoro-4-hydroxyphenyl)-N'-(2-phenylethyl)ethanediamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of N-(4-benzyloxy-3-fluorophenyl)-N′-(2-phenylethyl)ethanediamide (40 g, 100 mmol) and 38% hydrobromic acid in acetic acid (250 mL) was stirred at room temperature overnight. The resulting solid was filtered, washed with water and dried to give N-(3-fluoro-4-hydroxyphenyl)-N′-(2-phenylethyl)ethanediamide as a slightly yellow solid (30.6 g, 99% yield). 1H NMR (400 MHz, d6-DMSO): δ 10.60 (s, 1H), 9.02 (t, 1H), 7.70 (d, 1H), 7.47 (d, 1H), 7.32-7.20 (m, 3H), 6.91 (t, 1H), 3.43 (m, 2H), 2.81 (m, 2H); 13C NMR (100 MHz, d6-DMSO): δ 160.5, 158.8, 152.0, 149.6, 142.2, 139.8, 130.3, 129.3, 129.0, 126.8, 118.1, 117.4, 109.6, 109.3 IR (cm−1): 3279, 1653, 1518, 1456, 1279, 1190, 742, 696, 584; LC/MS (M+H=303).

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-538764184b744ed188bb664ea39a5bfd
Source dataset
uspto-grants-2009_08
Patent number
US07579473B2

Reaction notes

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