6-Bromo-2-naphthalenol → 4-(6-Hydroxynaphthalen-2-yl)benzoic acid

HRID 1771469Notes

Reaction equation

HRID 1771469 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.B([C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1)(O)O>>[OH:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1)[CH:11]=[CH:10]2

Participants

3

Reactant 2

HCID 271446-Bromo-2-naphthalenolHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 248273004-(6-Hydroxynaphthalen-2-yl)benzoic acidYield 7%

Conditions

Temperature
85 °C

Procedure

Followed the coupling procedure described in Example 3, starting from 6-bromonaphthalen-2-ol and 4-boronobenzoic acid, where the reaction was heated at 85° C. for 8 h. After the prep-HPLC purification, a further purification by silica gel column (PE:EA=7:1 to 4:1) gave the compound as a yellow solid (26 mg, 7%). 1H NMR (DMSO-d6 500 MHz TMS): δ 12.97 (brs, 1H), 9.91 (brs, 1H), 8.19 (s, 1H), 8.04 (d, J=8.0 Hz, 2H), 7.87-7.92 (m, 3H), 7.80 (m, 2H), 7.13-7.16 (m, 2H); MS (ESI): m/z 265.1 [M+1]+.

Workup

  1. customAfter the prep-HPLC purification
  2. customa further purification by silica gel column (PE:EA=7:1 to 4:1)

Sources & evidence

ORD record
ord-c010775db7ac497bb1cdb180d0177bfd
Source dataset
uspto-grants-2016_02
Patent number
US09249132B2

Reaction notes

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