Potassium Bromide → 5-Bromo-6-hydroxy-3'-trifluoromethyl-biphenyl-3-carboxylic acid (8-phenyl-octyl)-amide

HRID 1884751Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:44])[C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[C:20]([OH:33])=[C:19](C3C=CC=C(C(F)(F)F)C=3)[CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[K+].[Br-:46]>>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[C:20]([OH:33])=[C:19]([Br:46])[CH:18]=2)=[O:44])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 253877Potassium Bromide

HCID 22237600N-(8-phenyl-octyl)-3,5-bis(m-trifluoromethylphenyl)4hydroxy-benzamide

Product 1

HCID 538999065-Bromo-6-hydroxy-3'-trifluoromethyl-biphenyl-3-carboxylic acid (8-phenyl-octyl)-amide

Procedure

The title compound was prepared as a white gum (0.976 g, 58%) from N-(8-phenyl-octyl)-3,5-bis(m-trifluoromethylphenyl)-4-hydroxy-benzamide using a procedure similar to Example 191. 1H NMR (DMSO-d6) δ 9.84 (s, 1H); 8.42 (t, 1H); 8.04 (d, 1H); 7.85-7.67 (m, 5H); 7.26-7.10 (m, 5H); 3.21 (dd, 2H); 2.52 (t, 2H); 1.50 (m, 4H); 1.26 (m, 8H); IR (KBr) 3330, 2950, 2850, 1620, 1550, 1495, 1470, 1330, 1220, 1170, 1120, 1100, 1080 cm−1; mass spectrum [(+)APCI], m/z 549 (M+H)+; Anal. Calcd. for C28H29F3NO2: C, 61.32; H, 5.33; N, 2.55, Found: C, 61.02; H, 5.29; N, 2.51.

Sources & evidence

ORD record: ord-3104a772941f411090dee1ccfc715043
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06765021B2

Reaction notes

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