Chlorosuccinimide → HCID 10286369, compound

HRID 1830664Notes

Reaction equation

HRID 1830664 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([OH:20])[CH:14]=[CH:13]2.C1C(=O)N([Cl:28])C(=O)C1>C1COCC1>[Cl:28][C:16]1[C:17]2[C:12](=[CH:11][C:10]([C:3]3[C:2]([F:1])=[CH:7][C:6]([OH:8])=[CH:5][C:4]=3[F:9])=[CH:19][CH:18]=2)[CH:13]=[CH:14][C:15]=1[OH:20]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 10214708HCID 10214708, compound

Product 1

HCID 10286369HCID 10286369, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by reacting 6-(2,6-difluoro-4-hydroxyphenyl)-2-naphthol (510 mg, 1.86 mmol) and NCS (301 mg, 2.25 mmol) in THF (30 mL) according to Method C to yield 440 mg (77%) of yellowish solid: mp 213–214° C.; 1H NMR (acetone-d6): δ 6.71–6.78 (2H, m), 7.47 (1H, d, J=8.85 Hz), 7.76 (1H, dd, J=8.12 Hz, J=1.52 Hz), 7.97 (1H, d, J=8.90 Hz), 8.04 (1H, s), 8.29 (1H, d, J=8.80 Hz), 9.26 (1H, s), 9.60 (1H, s); MS (ESI) m/z 305/307 (M−H)−; HRMS: calcd for C16H9ClF2O2, 306.0259; found (ESI−), 306.01991 Anal. for C16H9ClF2O2.0.25 H2O:

Sources & evidence

ORD record
ord-ff66e1439c9e48268348555cea352a86
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Reaction notes

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