HCID 20827022, compound → HCID 22280061, compound

HRID 1591548Notes

Reaction equation

HRID 1591548 reaction equation
FC1C=C(F)C=CC=1COC1C=CC(CO)=CC=1.C[O:20][C:21](=[O:49])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([F:46])=[CH:42][C:41]=3[F:47])=[CH:34][CH:33]=2)=[CH:26][C:25]=1[CH3:48]>>[F:47][C:41]1[CH:42]=[C:43]([F:46])[CH:44]=[CH:45][C:40]=1[CH2:39][O:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][S:30][C:27]2[CH:28]=[CH:29][C:24]([O:23][CH2:22][C:21]([OH:49])=[O:20])=[C:25]([CH3:48])[CH:26]=2)=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 20827022HCID 20827022, compound2×HCID 22280034HCID 22280034, compound

Product 1

HCID 22280061HCID 22280061, compound

Procedure

Preparation of [4-(2,4-Difluoro-benzyloxy)phenyl]-methanol (compound 31A) The title compound was prepared in the manner analogous to Example 14A using 1-bromomethyl-2,4-difluoro-benzene and 4-hydroxymethyl-phenol. MS m/z 233 (M-OH). Step 2. Preparation of 1-(4-Chloromethyl-phenoxymethyl)-2,4-difluoro-benzene (compound 31B) The title compound was prepared in the manner analogous to Example 3B using 31A. MS m/z 233 (M-Cl). Step 3. Preparation of {4-[4-(2,4-Difluoro-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid methyl ester (compound 31C) The title compound was prepared in the manner analogous to Example 1F using 31B and 2C. MS m/z 445 (M+1). Step 4. Preparation of {4-[4-(2,4-Difluoro-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid To a solution of the product from Example 31C (1.5 g, 3.3 mmol) in a mixture of 20 mL of tetrahydrofuran and 4 mL of water was added lithium hydroxide monohydrate (0.42 g, 9.9 mmol). The reaction mixture was stirred at room temperature for 18 hrs and then evaporated to afford a residue, which was suspended in 50 mL of water. The mixture was acidified with 1N hydrochloric acid to pH 2. The precipitated solid was collected be filtration, washed with water, and then dried to provide the title compound without any further purification. mp 139-141° C.; IR (KBr) cm−1: 3081, 2917, 1735, 1604, 1508, 1233; 400 MHz 1H NMR (DMSO-d6): δ 7.51-7.59 (m, 1H), 7.02-7.31 (m, 6H), 6.85-6.92 (m, 2H), 6.68 (d, 1H, J=8.6 Hz), 5.01 (s, 2H), 4.60 (s, 2H), 4.00 (s, 2H), 2.08 (s, 3H); MS m/z 429 (M−1). Anal. Calc'd for C23H20F2O4S: C, 64.17; H, 4.68; found: C, 64.11; H, 4.59.

Workup

  1. customwas prepared in the manner analogous to Example 3B

Sources & evidence

ORD record
ord-1ec9ae3e3ed2440aba7076576e1178dd
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

Loading…