Chlorosuccinimide → HCID 10149610, compound

HRID 895216Notes

Reaction equation

HRID 895216 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([F:9])=[CH:4][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[CH:4]=[C:5]([F:9])[C:6]([OH:8])=[CH:7][C:2]=3[F:1])=[CH:19][CH:18]=2)[CH:13]=[CH:14][C:15]=1[OH:20]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 10308206HCID 10308206, compound

Product 1

HCID 10149610HCID 10149610, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by reacting 6-(2,5-difluoro-4-hydroxyphenyl)-2-naphthol (500 mg, 1.84 mmol) and NCS (295 mg, 2.21 mmol) in THF (37 mL) according to method C to yield 370 mg (66%) of yellowish solid: mp 203-204° C.; 1H NMR (DMSO-d6): δ 6.90 (1H, dd, J=11.90 Hz, J=7.50 Hz), 7.32 (1H, d, J=8.88 Hz), 7.49 (1H, dd, J=11.87 Hz, J=7.60 Hz), 7.72-7.76 (1H, m), 7.84 (1H, d, J=8.97 Hz), 8.03 (1H, s), 8.06 (1H, d, 8.87 Hz), 10.58 (2H, s); MS (ESI) m/z3051307 (M−H)−; HRMS calcd for C16H9ClF2O2 306.02591, observed 305.01863 (M−H)−.

Sources & evidence

ORD record
ord-912574b2ac0b4cfdb3ee4357fde7b7d8
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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