Water → HCID 18687797, compound

HRID 1873192Notes

Reaction equation

HRID 1873192 reaction equation
[Br:1][C:2]1[CH:27]=[C:26]([C:28]2[C:37]3[C:38]4[CH:44]=[CH:43][CH:42]=[CH:41][C:39]=4[S:40][C:36]=3[C:35]([Br:45])=[C:34]3[C:29]=2[CH:30]=[CH:31][CH:32]=[CH:33]3)[CH:25]=[C:24]([Br:46])[C:3]=1[O:4][CH:5]([CH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=1)[C:6]([O:8]C(C)(C)C)=[O:7].O.CCOCC>FC(F)(F)C(O)=O>[Br:46][C:24]1[CH:25]=[C:26]([C:28]2[C:37]3[C:38]4[CH:44]=[CH:43][CH:42]=[CH:41][C:39]=4[S:40][C:36]=3[C:35]([Br:45])=[C:34]3[C:29]=2[CH:30]=[CH:31][CH:32]=[CH:33]3)[CH:27]=[C:2]([Br:1])[C:3]=1[O:4][CH:5]([CH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 76121399HCID 76121399, compound

Product 1

HCID 18687797HCID 18687797, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-[2,6-dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy ]-3-naphthalen-2yl--propionic acid, tert butyl ester (0.221 g, 0.270 mmol) in trifluoroacetic acid (10 mL) was heated to 50° C. for 15 hours. The mixture was cooled to room temperature and combined with water. Ether was added and the resulting organic suspension was separated from the water layer and concentrated. The residue was dried in vacuo at 46 C. to provide the title compound as an off white solid (0.186 g, 90%) mp 270-271° C.; NMR (DMSO-d6); δ13.25 (broad singlet, 1 H), 8.28 (d, J=8 Hz, 1 H,), 8.06 (d, J=8 Hz, 1 H), 7.91(m, 4 H), 7.81(d, J=2 Hz, 1 H), 7.79(d, J =2 Hz, 1 H) 7.82-7.77(m, 1 H), 7.63-7.47(m, 6 H), 7.25 (dd, J=7, 1 Hz,, 1 H), 6.64 (d, J=8 Hz, 1 H) 5.42 (t, J=7 Hz, 1 H), 3.59 (d, J=7 Hz, 2 H); MS (FAB+): [M+], 3 bromine pattern, 757.8 (21%) 759.8 (100%) 761.8 (100%) 763.8 (50%); Anal. Calcd. for C31H19Br3O3S: C, 55.07; H,3.04, N, 0.00. Found: C, 55.36; H, 2.89, N, 0.06.

Workup

  1. customthe resulting organic suspension was separated from the water layer
  2. concentrationconcentrated
  3. customThe residue was dried in vacuo at 46 C

Sources & evidence

ORD record
ord-df979d2d73484a2caf602d8bf9e8fcf0
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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