Water → HCID 9831794, compound

HRID 1873191Notes

Reaction equation

HRID 1873191 reaction equation
C([O:5][C:6](=[O:43])[CH:7]([O:16][C:17]1[C:22]([Br:23])=[CH:21][C:20]([C:24]2[C:33]3[C:34]4[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=4[S:36][C:32]=3[C:31]([Br:41])=[C:30]3[C:25]=2[CH:26]=[CH:27][CH:28]=[CH:29]3)=[CH:19][C:18]=1[Br:42])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)(C)(C)C.O>FC(F)(F)C(O)=O>[Br:23][C:22]1[CH:21]=[C:20]([C:24]2[C:33]3[C:34]4[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=4[S:36][C:32]=3[C:31]([Br:41])=[C:30]3[C:25]=2[CH:26]=[CH:27][CH:28]=[CH:29]3)[CH:19]=[C:18]([Br:42])[C:17]=1[O:16][CH:7]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[C:6]([OH:43])=[O:5]

Participants

4

Reactant 2

HCID 962WaterHCID 54443209HCID 54443209, compound

Product 1

HCID 9831794HCID 9831794, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
55 °C

Procedure

A suspension of 2-[2,6-dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11 -yl)-phenoxy]-3-(4-fluoro-phenyl)-propionic acid tert-butyl ester (0.232 g 0.295 mmol) in trifluoroacetic acid (5 mL) was heated at 55° C. for 11 hours. After cooling to room temperature the reaction mixture was poured into water (60 mL) and extracted with ether. The combined ether extracts were washed with water and brine, concentrated, and dried in vacuo at 60° C. to provide the title compound as an off white solid (0.187 g, 98%): NMR (CDCl3); δ8.36 (d, J=7 Hz, 1 H), 7.82 (d, J=7 Hz, 1 H), 7.68 (ddd, J=8, 6, 2 Hz, 1 H), 7.58 (dd, J=8, 2 Hz, 2 H), 7.55-7.48 (m, 2 H), 7.45-7.35 (m, 3 H), 7.15 (dt, J=7, 1, 1H), 7.03 (tt J=10, 3, 1, 2H), 6.71 (d, J=8 Hz, 1 H), 5.44 (t, J=6 Hz, 1 H), 3.56 (d, J=7 Hz, 2 H); MS (+FAB): [M+], 3 bromine isotope pattern, 726 (15%), 728 ( 30%) 730 (35%) 732 (15%); Anal. Calc. for C31H18Br3FO3S: C, 51.06, H, 2.49, N, 0.00. Found: C, 50.80, H, 2.46, N, 0.10.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. extractionextracted with ether
  3. washThe combined ether extracts were washed with water and brine
  4. concentrationconcentrated
  5. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-cc258056fa6c49eab4e36d6af4b247cb
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

Loading…