{4-[(4-Fluorophenyl)methoxy]phenyl}methanol → HCID 22280142, compound
Reaction equation
FC1C=CC(COC2C=CC(CO)=CC=2)=CC=1.C[O:19][C:20](=[O:47])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)=[CH:33][CH:32]=2)=[CH:25][C:24]=1[CH3:46]>>[F:45][C:42]1[CH:41]=[CH:40][C:39]([CH2:38][O:37][C:34]2[CH:33]=[CH:32][C:31]([CH2:30][S:29][C:26]3[CH:27]=[CH:28][C:23]([O:22][CH2:21][C:20]([OH:47])=[O:19])=[C:24]([CH3:46])[CH:25]=3)=[CH:36][CH:35]=2)=[CH:44][CH:43]=1Participants
Procedure
Preparation of [4-(4-Fluoro-benzyloxy)-phenyl]-methanol (compound 57A) The title compound was prepared in the manner analogous to Example 14A using 1-bromomethyl-4-fluoro-benzene and 4-hydroxymethyl-phenol. MS m/z 215 (M-OH). Step 2. Preparation of 1-(4-Chloromethyl-phenoxymethyl)-4difluoro-benzene (compound 57B) The title compound was prepared in the manner analogous to Example 3B using 57A. MS m/z 215 (M-Cl). Step 3. Preparation of {4-[4-(4-Fluoro-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid methyl ester (compound 57C) The title compound was prepared in the manner analogous to Example 1F using 57B and 2C. MS m/z 427 (M+1). Step 4. Preparation of {4-[4-(4-Fluoro-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid (compound 57) The title compound was prepared in the manner analogous to Example 1 using the product from Example 57C. mp 154-155° C.; IR (KBr) cm−1: 3060, 2925, 1727, 1495, 1228, 1156; 400 MHz 1H NMR (DMSO-d6): δ 13.00 (br(s), 1H), 7.37-7.48 (m, 2H), 6.99-7.22 (m, 6H), 6.80-6.90 (m, 2H), 6.69 (d, 1H, J=8.5 Hz), 4.98 (s, 2H), 4.61 (s, 2H), 4.00 (s, 2H), 2.08 (s, 3H); MS m/z 411 (M−1). Anal. Calc'd for C23H21FO4S: C, 66.97; H, 5.13; found: C, 66.64; H, 4.88.
Workup
- customwas prepared in the manner analogous to Example 3B
Sources & evidence
- ORD record
- ord-65429d3fea714150b4f62b4070040ffc
- Source dataset
- uspto-grants-2007_11
- Patent number
- USRE039916E1
Reaction notes
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