Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → 4-(Adamantan-1-ylmethoxy)-3,5-dichlorobenzoic acid

HRID 1849711Notes

Reaction equation

HRID 1849711 reaction equation
F[C:2]12[CH2:12][C:6]3(F)[CH2:7][C:8](F)([CH2:10][C:4]([CH2:14][OH:15])([CH2:5]3)[CH2:3]1)[CH2:9]2.C12(CO)CC3CC(CC(C3)C1)C2.ClC1C(F)=CC(F)=C(C=1)C(O)=O.[Cl:40][C:41]1[CH:42]=[C:43]([CH:47]=[C:48]([Cl:51])[C:49]=1F)[C:44]([OH:46])=[O:45]>>[C:4]12([CH2:14][O:15][C:49]3[C:48]([Cl:51])=[CH:47][C:43]([C:44]([OH:46])=[O:45])=[CH:42][C:41]=3[Cl:40])[CH2:10][CH:8]3[CH2:7][CH:6]([CH2:12][CH:2]([CH2:9]3)[CH2:3]1)[CH2:5]2

Participants

5

Reactant 4

HCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 148764175-Chloro-2,4-difluorobenzoic acidHCID 199713033,5-Dichloro-4-fluorobenzoic acidHCID 57406555(3,5,7-Trifluoroadamantan-1-yl)methanol

Product 1

HCID 867035864-(Adamantan-1-ylmethoxy)-3,5-dichlorobenzoic acid

Procedure

Following the procedure as described in Example 274 step 1 and making variations as required to replace (3,5,7-trifluoroadamantan-1-yl)methanol with adamantan-1-ylmethanol and to replace 5-chloro-2,4-difluorobenzoic acid with 3,5-dichloro-4-fluorobenzoic acid, the title compound was obtained as a colorless solid (1.73 g, quant.): 1H NMR (300 MHz, DMSO-d6) δ 13.44 (br s, 1H), 7.86 (s, 2H), 3.53 (s, 2H), 1.99-1.90 (m, 3H), 1.73-1.57 (m, 12H); MS (ES−) m/z 353.2, 355.2 (M−1).

Sources & evidence

ORD record
ord-09a4a2ea3c0b41aa92feef0ed7c504c1
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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